Diethyl Ether → (E)-(6R,7R)-7-(2-bromo-acetylamino)-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1597708노트

반응식

HRID 1597708 반응식
[NH2:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6](/[CH:14]=[C:15]1/[C:16](=[O:28])[N:17]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[CH2:18][CH2:19]/1)=[C:7]2[C:11]([OH:13])=[O:12].C[Si](/N=C(/O[Si](C)(C)C)\C(F)(F)F)(C)C.[Br:44][CH2:45][C:46](Br)=[O:47].C(OCC)C>ClCCl>[Br:44][CH2:45][C:46]([NH:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6](/[CH:14]=[C:15]1/[C:16](=[O:28])[N:17]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=3)[CH2:18][CH2:19]/1)=[C:7]2[C:11]([OH:13])=[O:12])=[O:47]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 61147Bromoacetyl bromideHCID 5366669trimethylsilyl (1E)-2,2,2-trifluoro-N-trimethylsilylethanimidateHCID 69468538(E)-(6R,7R)-7-amino-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

생성물 1

HCID 69465125(E)-(6R,7R)-7-(2-bromo-acetylamino)-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(E)-(6R,7R)-7-amino-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (736.0 mg, 1.83 mmol) was suspended in 20 ml dichloromethane and N,O-bis(trimethylsilyl)-trifluoroacetamide (1.94 ml, 7.32 mmol) was added. After 45 min bromoacetyl bromide (167 ml, 1.92 mmol) was added dropwise. After 1 h the reaction mixture was poured on 200 ml diethyl ether containing 160 ml water. After 15 min the solid material was collected by filtration, washed with diethyl ether and dried in high vacuum.

후처리

  1. filtrationAfter 15 min the solid material was collected by filtration
  2. washwashed with diethyl ether
  3. customdried in high vacuum

출처 및 근거

ORD 기록
ord-d0f3e022672b4ebd91b3492f8433a36a
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06294668B1

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