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Hydrochloric Acid → HCID 131711282, compound

HRID 1764788
Notes
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Reaction equation

HRID 1764788 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([NH:15][C@H:16]([C:32]([OH:34])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[NH:43]([C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[C@H:44]([C:55]([O:57]N1C(=O)CCC1=O)=O)[C@@H:45]([CH3:54])[O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.CCN(CC)CC>C1COCC1.CN(C=O)C.CCN(CC)CC.O.CCOC(C)=O.CC(O)=O>[NH:43]([C:65]([O:67][C:68]([CH3:69])([CH3:70])[CH3:71])=[O:66])[C@H:44]([C:55]([NH:1][C@H:2]([C:13]([NH:15][C@H:16]([C:32]([OH:34])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:57])[C@@H:45]([CH3:54])[O:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12879029Boc-Thr(Bzl)-OSuHCID 131711283HCID 131711283, compound

Product 1

HCID 131711282HCID 131711282, compound

Reagents, catalysts & solvents 6

HCID 8471
Triethylamine
Catalyst
HCID 176Acetic AcidSolvent
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Boc-Thr(Bzl)-Lys(Z)-OH (14.0 g, 24.5 mmol) was treated with 500 ml of 4.0 N HCl in THF for 30 minutes, evaporated to dryness, and re-evaporated twice with fresh THF. The oily residue solidified when treated with ether. The dried powder (11.4 g, 21.6 mmol) of the dipeptide hydrochloride salt was then dissolved in 140 ml DMF, cooled to 0°, and treated with Boc-Thr(Bzl)-OSu (8.8 g, 21.6 mmol) followed by 3.5 ml of Et3N. A few drops of Et3N was added to maintain a slightly basic condition while the mixture was stirred for an additional 24 hours at 25°. It was acidified with 5 ml of HOAc and then diluted with a large volume of water. The solid crude product precipitated was collected, dissolved in EtOAc, washed with H2O, dried over Na2SO4, and evaporated to dryness, leaving a glassy solid mass. Crystallized from EtOAc and petroleum ether: yield, 13.8 g (83.7%); mp 110°- 112°; [α]D25 = +19.45° (c 1, EtOAc).

Workup

  1. customevaporated to dryness
  2. customre-evaporated twice with fresh THF
  3. additiontreated with ether
  4. temperaturecooled to 0°
  5. temperatureto maintain a slightly basic condition while the mixture
  6. customThe solid crude product precipitated
  7. customwas collected
  8. dissolutiondissolved in EtOAc
  9. washwashed with H2O
  10. dry with materialdried over Na2SO4
  11. customevaporated to dryness
  12. customleaving a glassy solid mass
  13. customCrystallized from EtOAc and petroleum ether
  14. customyield

Sources & evidence

ORD record
ord-874099034c7349b897219820e42ef54f
Source dataset
uspto-grants-1978_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04116951

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes