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Di-tert-butyl dicarbonate → (S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

HRID 1675244
ノート
印刷プレビュー

反応式

HRID 1675244 の反応式
[CH3:1][C:2](OC(OC(OC(C)(C)C)=O)=O)(C)C.[CH2:16]([C@H:23]1[CH2:27][O:26][C:25](=[O:28])[N:24]1[C:29](=[O:50])[CH2:30][C@@H:31]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:38][CH:37]=1)[CH2:32][N+:33]([O-])=[O:34])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.C(Br)=C>[CH2:16]([C@H:23]1[CH2:27][O:26][C:25](=[O:28])[N:24]1[C:29](=[O:50])[CH2:30][C@@H:31]([C:36]1[CH:37]=[CH:38][C:39]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[CH:40][CH:41]=1)[C:32]1[CH:2]=[CH:1][O:34][N:33]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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 2

HCID 90495Di-tert-butyl dicarbonate2 回HCID 57801835(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-4-nitrobutanoyl)oxazolidin-2-one

生成物 1

HCID 57801834(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one収率 93.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 11641
Bromoethene
溶媒

実験手順

(Boc)2O (6.9 g, 31.65 mmol) was added at room temperature to a solution of 7.3 (10 g, 21.1 mmol), vinyl bromide (230 mL, 1.0 M solution in THF), DMAP (256 mg, 2.1 mmol), and TEA (3.5 mL, 25.3 mmol). The mixture was stirred at room temperature for 2.5 days. During the reaction, more (Boc)2O (2 g twice) was added. After HPLC indicated that all 7.3 was consumed, the reaction mixture was taken into EtOAc (500 mL), and saturated sodium bicarbonate (400 mL) was added. The organic layer was separated, washed with brine, dried, and concentrated under vacuum. The crude product was taken into hot MeOH (70 mL). The mixture was stirred vigorously at 75° C. for 5 hours. The mixture was then cooled to room temperature and allowed to stand for 3 hours. The solid product was collected by filtration and washed with MeOH to give 7.4 (9.5 g). MS ESI (pos.) m/e: 483 (M+H). 1H NMR (CDCl3) δ 8.30 (d, 1H), 7.30 (m, 12H), 6.95 (d, 2H), 6.15 (d, 1H), 5.05 (s, 2H), 4.76 (dd, 1H), 4.64 (m, 1H), 4.15 (d, 2H), 4.05 (dd, 1H), 3.56 (dd, 1H), 3.23 (dd, 1H), 2.78 (dd, 1H).

後処理

  1. additionwas added
  2. customwas consumed
  3. additionwas added
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated under vacuum
  8. stirringThe mixture was stirred vigorously at 75° C. for 5 hours
  9. temperatureThe mixture was then cooled to room temperature
  10. waitto stand for 3 hours
  11. filtrationThe solid product was collected by filtration
  12. washwashed with MeOH

出典と根拠

ORDレコード
ord-b1d461094eaa41a3a196f427657f63cf
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08003648B2

反応ノート

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