Leucine, N-carboxy-, N-benzyl ester, L- → [(R)-3-((S)-2-Amino-4-methyl-pentanoylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid

HRID 1926987

反応式

HRID 1926987 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])[CH2:36][CH:37]([CH3:39])[CH3:38])(OCC1C=CC=CC=1)=O>>[NH2:34][C@@H:35]([CH2:36][CH:37]([CH3:39])[CH3:38])[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 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 68622110((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride

生成物 1

HCID 11617201[(R)-3-((S)-2-Amino-4-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 5 except for employing ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride and N-Cbz-L-leucine as the starting materials. Subsequent hydrogenation of the resulting benzyl ester in accordance with the procedures of Step 5, Method A of Example 1 yielded the title compound. 1H NMR (CD3OD, 300 MHz): δ 4.18-3.98 (m, 1H), 3.83 (t, 1H), 3.52-3.38 (m, 1H), 3.35-3.20 (m, 1H), 1.95 (br d, 2H), 1.83-1.58 (m, 9H), 1.52 (dd, 2H), 1.42-1.15 (m, 3H), 1.10-0.95 (m, 8H). 31P NMR (CD3OD, 300 MHz): δ 41. LCMS m/z: [M+H]+=349.2.

出典と根拠

ORDレコード
ord-fe044e6a885545df9820d342139fa1b7
出典データセット
uspto-grants-2012_05
特許番号
US08183231B2

関連ノート

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