Benzyloxycarbonylglycine → {(r)-3-[(s)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-2-hydroxy-propyl}-cyclohexylmethyl-phosphinic acid benzyl ester

HRID 72157Notes

Reaction equation

HRID 72157 reaction equation
[C:1]([NH:11][CH2:12][C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[CH2:17]([O:24][P:25]([CH2:34][C@H:35]([OH:45])[CH2:36][NH:37][C:38](=[O:44])[C@@H:39]([NH2:43])[CH:40]([CH3:42])[CH3:41])([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:24][P:25]([CH2:34][C@H:35]([OH:45])[CH2:36][NH:37][C:38](=[O:44])[C@@H:39]([NH:43][C:13](=[O:15])[CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH:40]([CH3:42])[CH3:41])([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:26])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 14349BenzyloxycarbonylglycineHCID 68621821[(r)-3-((s)-2-Amino-3-methyl-butyrylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride

Product 1

HCID 68621931{(r)-3-[(s)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-2-hydroxy-propyl}-cyclohexylmethyl-phosphinic acid benzyl ester

Procedure

The title compound was prepared substantially in a similar manner as in Step 1 of Example 10 using N-Cbz-glycine and [(R)-3-((S)-2-amino-3-methyl-butyrylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride as the starting materials. The title compound thus obtained was purified by SiO2 chromatography using 0-4% MeOH/CH2Cl2 as the eluent. 1H NMR (CD3OD, 300 MHz): δ 7.20-7.15 (m, 10H), 5.17 (s, 2H), 5.02 (m, 2H), 4.19 (d, 1H), 4.09 (m, 1H), 3.80 (s, 2H), 3.23-3.15 (m, 2H), 2.08 (m, 1H), 2.01-1.90 (m, 2H), 1.88-1.78 (m, 6H), 1.70-1.59 (m, 2H), 1.30-1.11 (m, 2H), 1.03 (m, 1H), 0.95-0.88 (m, 8H). 31P NMR (CD3OD, 300 MHz): δ 60.61, 59.94. LCMS m/z: [M+H]+=616.26.

Sources & evidence

ORD record
ord-3f1302d298174eff87d0a7bfb0e68957
Source dataset
uspto-grants-2014_09
Patent number
US08828974B2

Reaction notes

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