Water → HCID 131714161, compound

HRID 2164486Notes

Reaction equation

HRID 2164486 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:11]([NH:13][C@H:14]([C:23]([NH:25][C@H:26]([C:34]([NH:36][C@H:37]([C:44]([NH:46][C@H:47]([C:54]([NH:56][C@H:57]([C:67]([O:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)=[O:68])[CH2:58][CH2:59][C:60](=[O:66])[O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:55])[CH2:48][O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:45])[CH2:38][O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:35])[C@@H:27]([CH3:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:24])[CH2:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5])[CH3:3].[NH:76]([C:111]([O:113][C:114]([CH3:117])([CH3:116])[CH3:115])=[O:112])[C@H:77]([C:84]([NH:86][C@H:87]([C:96]([NH:98][C@H:99]([C:101](ON1C(=O)CCC1=O)=[O:102])[CH3:100])=[O:97])[CH2:88][C:89](=[O:95])[O:90][C:91]([CH3:94])([CH3:93])[CH3:92])=[O:85])[CH2:78][O:79][C:80]([CH3:83])([CH3:82])[CH3:81].CCN(CC)CC.O>CN(C=O)C>[NH:76]([C:111]([O:113][C:114]([CH3:115])([CH3:117])[CH3:116])=[O:112])[C@H:77]([C:84]([NH:86][C@H:87]([C:96]([NH:98][C@H:99]([C:101]([NH:1][C@H:2]([C:4]([NH:6][C@H:7]([C:11]([NH:13][C@H:14]([C:23]([NH:25][C@H:26]([C:34]([NH:36][C@H:37]([C:44]([NH:46][C@H:47]([C:54]([NH:56][C@H:57]([C:67]([O:69][C:70]1[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=1)=[O:68])[CH2:58][CH2:59][C:60](=[O:66])[O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:55])[CH2:48][O:49][C:50]([CH3:51])([CH3:52])[CH3:53])=[O:45])[CH2:38][O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:35])[C@@H:27]([CH3:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:24])[CH2:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:12])[CH:8]([CH3:9])[CH3:10])=[O:5])[CH3:3])=[O:102])[CH3:100])=[O:97])[CH2:88][C:89](=[O:95])[O:90][C:91]([CH3:94])([CH3:93])[CH3:92])=[O:85])[CH2:78][O:79][C:80]([CH3:81])([CH3:82])[CH3:83]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13501928HCID 13501928, compoundHCID 131714155HCID 131714155, compound

Product 1

HCID 131714161HCID 131714161, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of H-Ala-Val-Asp(OtBu)-Thr(tBu)-Ser(tBu)-Ser(tBu)-Glu(OtBu)-OC6H5 0.708 mmol) in DMF (34 mL) was cooled to 0° and Boc-Ser(tBu)-Asp(OtBu)-Ala-OSu 510 mg, 0.85 mmol, 1.2 eq) added. Stirring proceeded at 0° for 30 min and 25° for 17 h while the pH was maintained at ~8 by addition of Et3N. Water (150 mL) was added with stirring and the product was collected by filtration and dried in vacuo. The solid was washed with CH3OH (2×20 mL) and dried in vacuo. Yield: 586 mg (53.3%); mp >250°; [α]D25 -23.06° (c 1, TFE); Rf 0.51 (CHCl3 :MeOH:AcOH; 80-2-0.4); Rf 0.72 (CHCl3 :MeOH:AcOH; 80-5-2). Anal. calc. for C76H131N10O23 (1552.93): C, 58.78; H, 8.50; N, 9.01. Found: C, 58.65; H, 8.32; N, 8.93.

Workup

  1. stirringwith stirring
  2. filtrationthe product was collected by filtration
  3. customdried in vacuo
  4. washThe solid was washed with CH3OH (2×20 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-95d6688680d64babbe34a8dcc504f41e
Source dataset
uspto-grants-1985_03
Patent number
US04504415

Reaction notes

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