Carbon tetrabromide → N-Boc-beta-bromoalanine benzyl ester

HRID 495969

반응식

HRID 495969 반응식
[CH2:1]([O:8][C:9](=[O:21])[C@H:10]([CH2:19]O)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9](=[O:21])[C@H:10]([CH2:19][Br:23])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 7018792Boc-Ser-OBzl

생성물 1

HCID 11772725N-Boc-beta-bromoalanine benzyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

The N-Boc-serine benzyl ester was brought up in dichloromethane (170 mL) and treated with carbon tetrabromide (26.37 g, 79.51 mmol, 1.2 eq.), and triphenylphosphine (25.20 g, 96.08 mmol, 1.45 eq.) and the solution was stirred at 0° C. for 30 min. The volatiles were then evaporated in vacuo and the residue was triturated with ether (1000 mL). The solid that separated out was filtered off and organic layer was evaporated in vacuo to get the crude product. The crude material was purified by flash chromatography on silica gel to get N-Boc-β-bromoalanine benzyl ester.

후처리

  1. customThe volatiles were then evaporated in vacuo
  2. customthe residue was triturated with ether (1000 mL)
  3. customThe solid that separated out
  4. filtrationwas filtered off
  5. customorganic layer was evaporated in vacuo
  6. customto get the crude product
  7. customThe crude material was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-261e6dacfb0e404994c4a29fb1237969
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943157B2

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