Sodium triacetoxyborohydride → HCID 54338209、化合物

HRID 1780805

反応式

HRID 1780805 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[CH3:15])=[O:6].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:33]([O:37][C:38]([NH:40][C@H:41]([CH:63]=O)[CH2:42][S:43][C:44]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([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)=[O:39])([CH3:36])([CH3:35])[CH3:34]>ClCCCl>[C:33]([O:37][C:38]([NH:40][C@@H:41]([CH2:42][S:43][C:44]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[CH2:63][NH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[CH3:15])=[O:6])=[O:39])([CH3:34])([CH3:35])[CH3:36]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 64565863-amino-N-(2,3-dimethylphenyl)benzamideHCID 10388929N-Boc-S-trityl-(L)-cysteinal

生成物 1

HCID 54338209HCID 54338209、化合物

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
20 °C

実験手順

To a solution of 2 (0.28 g) in 12 mL of 1,2-dichloroethane at 0° C. was added sodium triacetoxyborohydride (0.36 g) and N-t-butyloxycarbonyl-S-(triphenyl- methyl)cysteinal (0.35 g). The cooling bath was removed and the mixture was stirred for 4 h at 20° C. The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was extracted with 50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a foam. NMR (300 MHz, CDCl3) δ 8.17 (1H, b), 7.46-7.18 (15H, m), 6.60 (1H, m), 3.13(2H, m,), 2.45(3H, m), 2.30 (3H, s), 2.18 (3H, s), 1.42 (9H, s).

後処理

  1. customThe cooling bath was removed
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe ethyl acetate layer was extracted with 50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-62f6a466590c4ce697af1f2b5e7f422b
出典データセット
uspto-grants-1997_05
特許番号
US05631280

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