18-Hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo[14.3.0.04,6]-nonadec-7-ene → 18-(2-Carbonylethoxyphenylaminocarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene

HRID 500409

반응식

HRID 500409 반응식
[OH:1][CH:2]1[CH2:20][CH:19]2[N:4]([C:5](=[O:39])[CH:6]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH:14]3[C:16]([C:22]([NH:24][S:25]([CH:28]4[CH2:30][CH2:29]4)(=[O:27])=[O:26])=[O:23])([NH:17][C:18]2=[O:21])[CH2:15]3)[CH2:3]1.C(=CCO[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[N:51]=[C:52]=[O:53])=O>>[C:7](=[CH:6][CH2:5][O:39][N:51]([C:46]1[CH:45]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:52]([O:1][CH:2]1[CH2:20][CH:19]2[N:4]([C:5](=[O:39])[CH:6]([NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH:14]3[C:16]([C:22]([NH:24][S:25]([CH:28]4[CH2:29][CH2:30]4)(=[O:26])=[O:27])=[O:23])([NH:17][C:18]2=[O:21])[CH2:15]3)[CH2:3]1)=[O:53])=[O:8]

참가 물질

3

반응물 2

HCID 7226012718-Hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo[14.3.0.04,6]-nonadec-7-eneHCID 866120872-Carbonylethoxyphenyl isocyanate

생성물 1

HCID 8661208618-(2-Carbonylethoxyphenylaminocarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene수율 27.1%

실험 절차

Prepared by way of method III using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.175 mmol) and 2-carbonylethoxyphenyl isocyanate (102 mg, 0.53 mmol). The final trituration (diethyl ether/hexane) and filtration gave 18 mg (14%) of 18-(2-carbonylethoxyphenylaminocarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 98.9% pure (HPLC), MS m/z 758 (M−H)−, HRMS: calcd. 760.3228 and found 760.3226 (M+NH4)+, mp 148-150° C.

후처리

  1. customPrepared by way of method III
  2. filtrationThe final trituration (diethyl ether/hexane) and filtration

출처 및 근거

ORD 기록
ord-3d104705b6e34eaea92712cf5b9c39e8
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772183B2

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