((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride → HCID 178448354, compound

HRID 72168Notes

Reaction equation

HRID 72168 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:32]([NH:34][C@H:35]([C:39](O)=[O:40])[CH:36]([CH3:38])[CH3:37])=[O:33])[CH2:26][C:27]1[N:31]=[CH:30][NH:29][CH:28]=1>>[NH2:24][C@@H:25]([CH2:26][C:27]1[N:31]=[CH:30][NH:29][CH:28]=1)[C:32]([NH:34][C@@H:35]([CH:36]([CH3:38])[CH3:37])[C:39]([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:40])=[O:33]

Participants

3

Reactant 2

HCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochlorideHCID 178448344HCID 178448344, compound

Product 1

HCID 178448354HCID 178448354, compound

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-His-Val-OH as the starting materials, which yielded the title compound as a white powder. 1H NMR (CD3OD, 300 MHz): δ 8.47 (s, 1H), 7.25 (s, 1H), 4.25 (t, 1H), 4.10 (d, 1H), 4.0 (m, 1H), 3.6-3.5 (dd, 1H), 3.10-3.00 (m, 2H), 2.09-2.02 (m, 1H), 1.95-1.86 (m, 2H), 1.80-1.54 (m, 8H), 1.41-1.02 (m, 3H), 1.0-0.95 (m, 9H). 31P NMR (CD3OD, 300 MHz): δ 42.66. LCMS m/z: [M+H]+=472.

Workup

  1. customThe title compound was prepared substantially

Sources & evidence

ORD record
ord-7b29501bf32f49cdae6528b0b8342999
Source dataset
uspto-grants-2014_09
Patent number
US08828974B2

Reaction notes

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