benzyl N-[(1S)-3-amino-1-[[1-benzyl-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenyl-butyl]carbamoyl]-3-oxo-propyl]carbamate → 2-Amino-4-(Cbz-asparaginyl-amino)-1,5-diphenyl-3-hydroxypentane

HRID 1078111Notes

Reaction equation

HRID 1078111 reaction equation
C(OC([NH:8][CH:9]([CH:17]([OH:45])[CH:18]([NH:26][C:27](=[O:44])[C@H:28]([CH2:40][C:41](=[O:43])[NH2:42])[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:45])[CH:18]([NH:26][C:27](=[O:44])[C@H:28]([CH2:40][C:41](=[O:43])[NH2:42])[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 3011024benzyl N-[(1S)-3-amino-1-[[1-benzyl-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenyl-butyl]carbamoyl]-3-oxo-propyl]carbamateHCID 22281272Methanol isopropylamine chloroform

Product 1

HCID 228455872-Amino-4-(Cbz-asparaginyl-amino)-1,5-diphenyl-3-hydroxypentaneYield 95%

Procedure

Using the procedure of Example 11 with the resultant compound of Example 66 gave, after silica gel chromatography using methanol/isopropylamine/chloroform, the desired compound (RF 0.3; 2.5% methanol/2% isopropylamine/chloroform) in 95% yield. Mass spectrum (M+H)+ =519.

Workup

  1. customgave

Sources & evidence

ORD record
ord-59f0524659054cf5b4ea00ca86203eff
Source dataset
uspto-grants-1996_08
Patent number
US05545750

Reaction notes

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