Methanol → 2-(Boc-valinyl-amino)-4-(Cbz-valinyl-amino)-1,5-diphenyl-3-hydroxypentane

HRID 1078136Notes

Reaction equation

HRID 1078136 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:16][CH:17]([CH:25]([OH:52])[CH:26]([NH:34][C:35](=[O:51])[C@H:36]([CH:48]([CH3:50])[CH3:49])[NH:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N=C=N.CO>C(Cl)(Cl)Cl>[C:1]([NH:8][C@H:9]([C:13]([NH:16][CH:17]([CH:25]([OH:52])[CH:26]([NH:34][C:35](=[O:51])[C@H:36]([CH:48]([CH3:50])[CH3:49])[NH:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:15])[CH:10]([CH3:11])[CH3:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 83693Boc-L-ValineHCID 160435CarbodiimideHCID 228644462Amino-4-(Cbz-valinyl-amino)-1,5-diphenyl-3hydroxypentane

Product 1

HCID 228455912-(Boc-valinyl-amino)-4-(Cbz-valinyl-amino)-1,5-diphenyl-3-hydroxypentane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Boc-valine was coupled to the resultant compound of Example 69 using the carbodiimide coupling procedure of Example 55 to provide, after silica gel chromatography using 3% methanol in chloroform, the desired compound (82%, Rf 0.7, 10% methanol in chloroform) as a white solid, m.p. 184°-184° C. Mass spectrum: (M+H)+ =703.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-e6a60cf613c5427883032e748022c780
Source dataset
uspto-grants-1996_08
Patent number
US05545750

Reaction notes

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