Benzyl chloroformate → (7S,10S,13S)-13-Benzyloxycarbonylamino-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo-[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester

HRID 2371327

반응식

HRID 2371327 반응식
Cl.[CH3:2][O:3][C:4]([C@H:6]1[NH:22][C:21](=[O:23])[C@H:20](C(C)C)[NH:19][C:18](=[O:27])[C@@H:17]([NH2:28])[CH2:16][C:15]2=[CH:29][CH:30]=[C:12]([CH:13]=[CH:14]2)[O:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].CCN([CH:48]([CH3:50])[CH3:49])C(C)C.[CH3:51]COC(C)=O.C(Cl)Cl>CN(C=O)C>[CH3:2][O:3][C:4]([C@H:6]1[NH:22][C:21](=[O:23])[C@H:20]([CH2:49][CH:48]([CH3:50])[CH3:51])[NH:19][C:18](=[O:27])[C@@H:17]([NH:28][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:16][C:15]2=[CH:29][CH:30]=[C:12]([CH:13]=[CH:14]2)[O:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]

참가 물질

6

반응물 4

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 21226138Dichloromethane ethylacetateHCID 86650244(7S,10S,13S)-13-Amino-10-isopropyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1-(18),15(19),16-triene-7-carboxylic acid methyl ester hydrogen chloride salt

생성물 1

HCID 44191155(7S,10S,13S)-13-Benzyloxycarbonylamino-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo-[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Amine 47 (65 mg) was dissolved in anhydrous DMF (30 mL). Benzyl chloroformate (0.29 mL) and DIPEA (0.75 mL) were added and the reaction mixture was stirred at rt for 18 h before being partitioned between chloroform and 1M hydrochloric acid. The aqueous phase was extracted three more times with chloroform and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 15% EtOAc/DCM to 50% EtOAc/DCM to yield an off-white solid, 54 mg, 70%. Rf=0.33 (30% EtOAc/DCM).

후처리

  1. custombefore being partitioned between chloroform and 1M hydrochloric acid
  2. extractionThe aqueous phase was extracted three more times with chloroform
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. washeluting with a gradient of 15% EtOAc/DCM to 50% EtOAc/DCM
  8. customto yield an off-white solid, 54 mg, 70%

출처 및 근거

ORD 기록
ord-028affbd831f4a298fda6f3bde9da8b2
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710178B2

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