tert-butyl N-[1-benzyl-3-[[(2S)-2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]-2-hydroxy-4-phenyl-butyl]carbamate → 2Amino-4-(Cbz-valinyl-amino)-1,5-diphenyl-3hydroxypentane

HRID 1379360Notes

Reaction equation

HRID 1379360 reaction equation
C(OC([NH:8][CH:9]([CH:17]([OH:44])[CH:18]([NH:26][C:27](=[O:43])[C@H:28]([CH:40]([CH3:42])[CH3:41])[NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)(C)(C)C.CO.C(N)(C)C.C(Cl)(Cl)Cl>>[NH2:8][CH:9]([CH:17]([OH:44])[CH:18]([NH:26][C:27](=[O:43])[C@H:28]([CH:40]([CH3:42])[CH3:41])[NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 3011021tert-butyl N-[1-benzyl-3-[[(2S)-2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]-2-hydroxy-4-phenyl-butyl]carbamateHCID 22281272Methanol isopropylamine chloroform

Product 1

HCID 228644462Amino-4-(Cbz-valinyl-amino)-1,5-diphenyl-3hydroxypentaneYield 100%

Procedure

Using the procedure of Example 56 with the resultant compound of Example 55 gave, after silica gel chromatography using methanol/isopropylamine/chloroform, the desired compound (RF 0.3; 2.5% methanol/2% isopropylamine/chloroform) in 100% yield, m.p. 158°-160° C. Mass spectrum (M+H)+ =504.

Workup

  1. customgave

Sources & evidence

ORD record
ord-dc462c89c3f54676ac3c398a6f4e3529
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

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