N-[(Phenylmethoxy)carbonyl]-L-isoleucine → [(R)-3-((S)-2-Amino-3-methyl-pentanoylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

HRID 72154

反応式

HRID 72154 の反応式
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.C([NH:34][C@H:35]([C:40](O)=[O:41])[C@H:36]([CH2:38][CH3:39])[CH3:37])(OCC1C=CC=CC=1)=O>>[NH2:34][C@@H:35]([CH:36]([CH3:37])[CH2:38][CH3:39])[C:40]([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:41]

参加物

3

反応物 2

HCID 2724772N-[(Phenylmethoxy)carbonyl]-L-isoleucineHCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride

生成物 1

HCID 11617202[(R)-3-((S)-2-Amino-3-methyl-pentanoylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

実験手順

Step 4, Method B of Example 1 was substantially repeated in this Example 6 except for employing ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride and N-Cbz-L-isoleucine as the starting materials. Subsequent hydrogenation of the resulting benzyl ester in accordance with the procedures of Step 5, Method A of Example 1 and RP-HPLC purification yielded the title compound. 1H NMR (CD3OD, 300 MHz): δ 4.18-4.03 (m, 1H), 3.72 (d, 1H), 3.40-3.35 (m, 2H), 2.01-1.85 (m, 5H), 1.80-1.50 (m, 7H), 1.42-1.18 (m, 4H), 1.17-0.95 (m, 8H). 31P NMR (CD3OD, 300 MHz): δ 53.18. LCMS m/z: [M+H]+=349.2.

後処理

  1. customSubsequent hydrogenation of the resulting benzyl ester in accordance with the procedures of Step 5, Method A of Example 1 and RP-HPLC purification

出典と根拠

ORDレコード
ord-6efeab7851b04a929b643f1a6da23927
出典データセット
uspto-grants-2014_09
特許番号
US08828974B2

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