((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride → ((r)-3-{(s)-2-[(s)-2-Amino-3-(1h-indol-3-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid

HRID 72162Notes

Reaction equation

HRID 72162 reaction equation
Cl.C([O:9][P:10]([CH2:19][C@H:20]([OH:23])[CH2:21][NH2:22])([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11])C1C=CC=CC=1.[NH:24](C(OCC1C=CC=CC=1)=O)[C@H:25]([C:36]([NH:38][C@H:39]([C:43](O)=[O:44])[CH:40]([CH3:42])[CH3:41])=[O:37])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1>>[NH2:24][C@@H:25]([CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[C:36]([NH:38][C@@H:39]([CH:40]([CH3:41])[CH3:42])[C:43]([NH:22][CH2:21][C@@H:20]([OH:23])[CH2:19][P:10]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)(=[O:11])[OH:9])=[O:44])=[O:37]

Participants

3

Reactant 2

HCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochlorideHCID 90473044Z-Trp-val-OH

Product 1

HCID 11584435((r)-3-{(s)-2-[(s)-2-Amino-3-(1h-indol-3-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid

Procedure

The title compound was prepared substantially following the procedures as set forth in Method B, Example 12, and employing ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride and N-Cbz-Trp-Val-OH as the staring materials, which yielded the title compound as a white powder. 1H NMR (CD3OD, 300 MHz): δ 7.65-7.62 (d, 1H), 7.38-7.35 (d, 1H), 7.17-7.01 (m, 3H), 4.26-4.20 (m, 1H), 4.17-4.14 (d, 1H), 4.05 (m, 1H), 3.46-3.20 (m, 4H), 2.00 (m, 1H), 1.9-1.88 (m, 2H), 1.77-1.54 (m, 8H), 1.34-1.16 (m, 3H), 1.05-0.94 (m, 8H). 31P NMR (CD3OD, 300 MHz): δ 42.89. LCMS m/z: [M+H]+=521.

Workup

  1. customThe title compound was prepared substantially

Sources & evidence

ORD record
ord-01f51136993c4de39a6df174fd2cfe86
Source dataset
uspto-grants-2014_09
Patent number
US08828974B2

Reaction notes

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