Sodium Hydroxide → HCID 178462158, compound

HRID 1289335Notes

Reaction equation

HRID 1289335 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([NH:12][C@H:13]([C:15]([NH:17][C@H:18]([C:27]([NH:29][C@H:30]([C:33]([N:35]1[CH2:174][CH2:173][CH2:172][C@H:36]1[C:37]([NH:39][C@H:40]([C:62]([NH:64][C@H:65]([C:89]([N:91]1[CH2:171][CH2:170][CH2:169][C@H:92]1[C:93]([NH:95][C@H:96]([C:122]([NH:124][C@H:125]([C:138]([NH:140][CH2:141][C:142]([N:144]1[CH2:168][CH2:167][CH2:166][C@H:145]1[C:146]([NH:148][C@H:149]([C:151]([NH:153][C@H:154]([C:162]([O:164]C)=[O:163])[C@@H:155]([CH3:161])[O:156]C(C)(C)C)=[O:152])[CH3:150])=[O:147])=[O:143])=[O:139])[CH2:126][CH2:127][CH2:128][CH2:129][NH:130]C(OC(C)(C)C)=O)=[O:123])[CH2:97][C:98]1[N:102]=[CH:101][N:100](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:99]=1)=[O:94])=[O:90])[CH2:66][C:67](=[O:88])[NH:68]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:63])[CH2:41][CH2:42][CH2:43][NH:44][C:45](=[NH:61])[NH:46]S(C1C(C)=C(C)C(OC)=CC=1C)(=O)=O)=[O:38])=[O:34])[CH2:31][SH:32])=[O:28])[CH2:19][C:20](=[O:26])[O:21]C(C)(C)C)=[O:16])[CH3:14])=[O:11])[C@@H:3]([CH3:9])[O:4]C(C)(C)C.[OH-].[Na+]>CO.O1CCOCC1>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:15]([NH:17][C@H:18]([C:27]([NH:29][C@H:30]([C:33]([N:35]1[CH2:174][CH2:173][CH2:172][C@H:36]1[C:37]([NH:39][C@H:40]([C:62]([NH:64][C@H:65]([C:89]([N:91]1[CH2:171][CH2:170][CH2:169][C@H:92]1[C:93]([NH:95][C@H:96]([C:122]([NH:124][C@H:125]([C:138]([NH:140][CH2:141][C:142]([N:144]1[CH2:168][CH2:167][CH2:166][C@H:145]1[C:146]([NH:148][C@H:149]([C:151]([NH:153][C@H:154]([C:162]([OH:164])=[O:163])[C@@H:155]([CH3:161])[OH:156])=[O:152])[CH3:150])=[O:147])=[O:143])=[O:139])[CH2:126][CH2:127][CH2:128][CH2:129][NH2:130])=[O:123])[CH2:97][C:98]1[N:102]=[CH:101][NH:100][CH:99]=1)=[O:94])=[O:90])[CH2:66][C:67](=[O:88])[NH2:68])=[O:63])[CH2:41][CH2:42][CH2:43][NH:44][C:45](=[NH:46])[NH2:61])=[O:38])=[O:34])[CH2:31][SH:32])=[O:28])[CH2:19][C:20](=[O:21])[OH:26])=[O:16])[CH3:14])=[O:11])[C@@H:3]([CH3:9])[OH:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 16183848HCID 16183848, compound

Product 1

HCID 178462158HCID 178462158, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

0.3 g of BOC-Thr(But)-Ala-Asp(OBut)-Cys-Pro-Arg(Mtr)-Asn(Trt)-Pro-His(Trt)-Lys(Boc)-Gly-Pro-Ala-Thr(But)-OMe (SEQ ID NO:111) is dissolved in 30 ml of methanol; 1.5 ml of 2N NaOH solution are added and the mixture is stirred at 250 for 4 hours. After removal of the solvent, the residue is taken up in water, the pH is adjusted to 3 by adding diluted HCI, and the product is extracted with ethyl acetate. The extract is dried over Na2 SO4. After removal of the solvent, BOC-Thr(But)-Ala-Asp(OBut)-Cys-Pro-Arg(Mtr)-Asn(Trt)-Pro-His(Trt)-Lys(Boc)-Gly-Pro-Ala-Thr(But)-OH (SEQ ID NO:112) is obtained, which is taken up in 20 ml of 2N Hcl in dioxane and stirred at room temperature for 2 hours. The reaction mixture is concentrated to dryness and the residue is taken up in TFA/CH2Cl2, precipitated with Et2O and purified by RP-H PLC, to give H-Thr-Ala-Asp-Cys-Pro-Arg-Asn-Pro-His-Lys-Gly-Pro-Ala-Thr-OH (SEQ ID NO:113); Rt=12.6; M+ =1465.

Workup

  1. customAfter removal of the solvent
  2. additionby adding
  3. additiondiluted HCI
  4. extractionthe product is extracted with ethyl acetate
  5. customThe extract is dried over Na2 SO4
  6. customAfter removal of the solvent, BOC-Thr(But)-Ala-Asp(OBut)-Cys-Pro-Arg(Mtr)-Asn(Trt)-Pro-His(Trt)-Lys(Boc)-Gly-Pro-Ala-Thr(But)-OH (SEQ ID NO
  7. custom112) is obtained
  8. stirringstirred at room temperature for 2 hours
  9. concentrationThe reaction mixture is concentrated to dryness
  10. customprecipitated with Et2O
  11. custompurified by RP-H PLC

Sources & evidence

ORD record
ord-3dbefca8cac645f3b3ada75cacf663be
Source dataset
uspto-grants-1998_05
Patent number
US05747457

Reaction notes

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