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Sodium cyanoborohydride → 4-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl ester

HRID 1739153
ノート
印刷プレビュー

反応式

HRID 1739153 の反応式
Cl.[CH3:2][O:3][C:4](=[O:26])[C@H:5]([CH2:22][CH2:23][S:24][CH3:25])[NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:27]([NH:34][C@H:35]([CH:57]=O)[CH2:36][S:37][C:38]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C([BH3-])#N.[Na+]>CO>[CH3:2][O:3][C:4](=[O:26])[C@H:5]([CH2:22][CH2:23][S:24][CH3:25])[NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:57][C@@H:35]([NH:34][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH2:36][S:37][C:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[CH:10][C:9]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 10388929N-Boc-S-trityl-(L)-cysteinalHCID 69612387(4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochloride

生成物 1

HCID 183929264-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl ester収率 67%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

To a mixture of 4-amino-2-phenylbenzoyl-(S)-methionine methyl ester hydrochloride (1.27 g, 3.22 mmol) in 20 mL of methanol was added N-Boc-S-trityl-(L)-cysteinal (1.0 eq, according to 1H NMR determination of aldehyde percentage) and sodium cyanoborohydride (400 mg, 2.0 eq). The mixture was stirred for 12 hr. After the evaporation of solvents, the residue was extracted with ethyl acetate and concentrated sodium bicarbonate. After removing solvents, the residue was purified through flash column chromatography (1:1=hexane:ethyl acetate, silica) to give the product 1.67 g (yield 67%). 1H NMR (CDCl3) δ 7.65 (d, 8.6 Hz, 1H), 7.34-7.42 (m, 11H), 7.18-7.29 (m, 9H), 6.52 (dd, 2.3 and 8.1 Hz, 1H), 6.34 (d, 2.3 Hz, 1H), 5.65 (d, 7.7 Hz, 1H), 4.64 (ddd, 1H), 4.55 (d, 8.1 Hz, 1H), 4.19 (br t, 1H), 3.78 (br m, 1H), 3.64 (s, 3H), 3.09 (t, 6.1 Hz, 2H), 2.44 (m, 2H), 2.04-2.10 (m, 2H), 2.00 (s, 3H), 1.81-1.90 (m, 1H), 1.60-1.70 (m, 1H), 1.41 (s, 9H); 13C NMR (CDCl3) δ 172.0, 168.3, 155.7, 149.4, 144.3, 141.6, 141.1, 131.3, 129.5, 128.7, 128.5, 127.9, 127.7, 126.8, 122.6, 113.6, 111.3, 79.8, 67.1, 52.2, 51.7, 49.5, 47.2, 34.3, 31.6, 29.4, 28.2, 15.2.

後処理

  1. customAfter the evaporation of solvents
  2. extractionthe residue was extracted with ethyl acetate and concentrated sodium bicarbonate
  3. customAfter removing solvents
  4. customthe residue was purified through flash column chromatography (1:1=hexane:ethyl acetate, silica)

出典と根拠

ORDレコード
ord-ac5840a81c124e2cbd456546ed7fcac6
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05965539

反応ノート

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