N-(benzyloxycarbonyloxy)succinamide → HCID 57512771, 화합물

HRID 857262

반응식

HRID 857262 반응식
Cl.[CH2:2]([C@H:9]([NH:23][C:24](=[O:33])[O:25]CC1C=CC=CC=1)[C@H:10]([OH:22])[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:34](OC(ONC(=O)CCC(N)=O)=O)[C:35]1[CH:40]=CC=C[CH:36]=1>C1COCC1>[CH2:2]([C@H:9]([NH:23][C:24](=[O:33])[O:25][C:35]([CH3:40])([CH3:36])[CH3:34])[C@H:10]([OH:22])[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 21865880N-(benzyloxycarbonyloxy)succinamideHCID 86617171HCID 86617171, 화합물

생성물 1

HCID 57512771HCID 57512771, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

tert-Butyl (1S, 2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate (VII, PREPARATION 8, 19.2 g, 48 mmole) in THF (100 ml). The reaction mixture is cooled to 0° and treated with N-benzyloxy carbonyloxysuccinamide (11.9 g, 48 mmole) while maintaining temperature <5°. The reaction mixture is stirred overnight and in the morning is concentrated under reduced pressure. The residue is partitioned between ethyl acetate and saturated aqueous bicarbonate. The organic phase is separated and washed with citric acid (5%), saline, dried over sodium sulfate and concentrated. The crude product is purified by preparatory HPLC eluting with a gradient of from 20/80–50/50 ethyl acetate. To give the title compound, M+H=534.

후처리

  1. temperatureThe reaction mixture is cooled to 0°
  2. temperaturewhile maintaining temperature <5°
  3. concentrationis concentrated under reduced pressure
  4. customThe residue is partitioned between ethyl acetate and saturated aqueous bicarbonate
  5. customThe organic phase is separated
  6. washwashed with citric acid (5%), saline
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude product is purified by preparatory HPLC
  10. washeluting with a gradient of from 20/80–50/50 ethyl acetate

출처 및 근거

ORD 기록
ord-ee69ec2539d0460f9ceb3374822ebe74
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144897B2

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