3-Methoxybenzoic Acid → 4-(5-Fluoro-2,3-dihydro-indol-1-yl)-3-(S)-[2-(S)-(3-methoxy-benzoylamino)-4,4-dimethyl-pentanoylamino]-butyric acid tert-butyl ester

HRID 132145

反応式

HRID 132145 の反応式
[C:1]([O:5][C:6](=[O:40])[CH2:7][C@H:8]([NH:20][C:21](=[O:39])[C@@H:22]([NH:28][C:29](OCC1C=CC=CC=1)=[O:30])[CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)[C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH3:49])[CH:43]=1>>[C:1]([O:5][C:6](=[O:40])[CH2:7][C@H:8]([NH:20][C:21](=[O:39])[C@@H:22]([NH:28][C:29](=[O:30])[C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH3:49])[CH:43]=1)[CH2:23][C:24]([CH3:27])([CH3:25])[CH3:26])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)([CH3:2])([CH3:4])[CH3:3]

参加物

3

反応物 2

HCID 114613-Methoxybenzoic AcidHCID 691960933-(S)-(2-(S)-Benzyloxycarbonylamino-4,4-dimethyl-pentanoylamino)-4-(5-fluoro-2,3-dihydro-indol-1-yl)-butyric acid tert-butyl ester

生成物 1

HCID 691960924-(5-Fluoro-2,3-dihydro-indol-1-yl)-3-(S)-[2-(S)-(3-methoxy-benzoylamino)-4,4-dimethyl-pentanoylamino]-butyric acid tert-butyl ester収率 92%

実験手順

This material was prepared in 92% yield in an analogous fashion to example 158 except that 3-(S)-(2-(S)-Benzyloxycarbonylamino-4,4-dimethyl-pentanoylamino)-4-(5-fluoro-2,3-dihydro-indol-1-yl)-butyric acid tert-butyl ester was deprotected and m-anisic acid was used as the acid; 1H NMR (CDCl3, 400 MHz) δ 0.95 (s, 9H), 1.40 (s, 9H), 1.57 (dd, 1H, J1=8.5, J2=14.5), 1.88 (dd, 1H, J1=4.0, J2=14.5), 2.51 (dd, 1H, J1=5.9, J2=16.3), 2.61 (dd, 1H, J1=5.1, J2=16.3), 2.81-2.96 (m, 2H), 3.07 (dd, 1H, J1=7.4, J2=13.8), 3.22 (dd, 1H, J1=6.5, J2=13.8), 3.34 (dd, 1H, J1=8.5, J2=17.1), 3.44 (dd, 1H, J=8.6, J2=16.3), 3.82 (s, 3H), 4.34-4.43 (m, 1H), 4.64 (ddd, 1H, J=4.0, J2=J3=8.5), 6.39 (dd, 1H, J=4.1, J2=8.5), 6.57 (d, 1H, J=8.4), 6.66-6.75 (m, 1H), 6.73-6.78 (m, 1H), 6.97 (d, 1H, J=8.5), 6.98-7.04 (m, 1H), 7.23-7.33 (m, 3H); HPLC-MS calcd. for C31H42FN3O5 (M+H+) 556.3, found 556.5.

出典と根拠

ORDレコード
ord-8896090210b347cc9692ef6ffb2b7c49
出典データセット
uspto-grants-2008_06
特許番号
US07384970B2

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