Z-Tyr-val-OH → ((r)-3-{(s)-2-[(s)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid

HRID 72163Notes

Reaction equation

HRID 72163 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:34]([NH:36][C@H:37]([C:41](O)=[O:42])[CH:38]([CH3:40])[CH3:39])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1>>[NH2:24][C@@H:25]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)[C:34]([NH:36][C@@H:37]([CH:38]([CH3:39])[CH3:40])[C:41]([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:42])=[O:35]

Participants

3

Reactant 2

HCID 6992485Z-Tyr-val-OHHCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride

Product 1

HCID 11526150((r)-3-{(s)-2-[(s)-2-Amino-3-(4-hydroxy-phenyl)-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-Tyr-Val-OH as the starting materials, which yielded the title compound as a white powder. 1H NMR (CD3OD, 300 MHz): δ 7.06 (d, 2H), 6.75 (d, 2H), 4.15-4.06 (m, 2H), 3.18-3.10 (m, 2H), 3.0-2.9 (m, 1H), 2.09-2.02 (m, 1H), 1.92-1.88 (m, 2H), 1.86-1.61 (m, 6H), 1.56-1.50 (m 3H), 1.30-1.17 (m, 4H), 1.06-0.95 (m, 8H). 31P NMR (CD3OD, 300 MHz): δ 41.72. LCMS m/z: [M+H]+=498.

Workup

  1. customThe title compound was prepared substantially

Sources & evidence

ORD record
ord-7d49eacc6b3d4086a7e82c3efceb2b64
Source dataset
uspto-grants-2014_09
Patent number
US08828974B2

Reaction notes

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