Cyclopropanesulfonic Acid → [2-(4-Ethyl-thiazol-2-yl)-5-methyl-phenyl]-carbamic acid 13-methyl-4-(1-methyl-cyclopropanesulphonylaminocarbonyl)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-en-17-yl ester

HRID 1445416Notes

Reaction equation

[CH2:1]([N:7]([CH3:51])[C:8]([CH:10]1[CH:14]([C:15](=[O:32])[NH:16][C:17]2([C:22]([NH:24][S:25]([C:28]3([CH3:31])[CH2:30][CH2:29]3)(=[O:27])=[O:26])=[O:23])[CH2:19][CH:18]2C=C)[CH2:13][CH:12]([O:33][C:34](=[O:50])[NH:35][C:36]2[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][C:37]=2[C:43]2[S:44][C:45](CC)=[CH:46][N:47]=2)[CH2:11]1)=[O:9])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[CH:52]1(S(O)(=O)=O)C[CH2:53]1>>[CH3:51][N:7]1[C:8](=[O:9])[CH:10]2[CH:14]([CH2:13][CH:12]([O:33][C:34](=[O:50])[NH:35][C:36]3[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][C:37]=3[C:43]3[S:44][CH:45]=[C:46]([CH2:52][CH3:53])[N:47]=3)[CH2:11]2)[C:15](=[O:32])[NH:16][C:17]2([C:22]([NH:24][S:25]([C:28]3([CH3:31])[CH2:30][CH2:29]3)(=[O:26])=[O:27])=[O:23])[CH:19]([CH2:18]2)[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2][CH2:1]1

Participants

Reactant 2

HCID 10419166Cyclopropanesulfonic Acid

HCID 66871250[2-(5-Ethyl-thiazol-2-yl)-5-methyl-phenyl]-carbamic acid 3-(hex-5-enyl-methyl-carbamoyl)-4-[1-(1-methyl-cyclopropanesulfonylamino-carbonyl)-2-vinyl-cyclopropylcarbamoyl]-cyclopentyl ester

Product 1

HCID 68676551[2-(4-Ethyl-thiazol-2-yl)-5-methyl-phenyl]-carbamic acid 13-methyl-4-(1-methyl-cyclopropanesulphonylaminocarbonyl)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-en-17-yl esterYield 10%

Procedure

The procedure described in Example 18-10 was followed, but using the compound prepared in Example 22 (112) (22 mg, 30 μmol) instead of the corresponding cyclopropanesulphonic acid derivative, which gave the title compound (2.1 mg, 10%). LC/MS (Method I): tr=2.41 min, >95%, m/z (ESI+)=712 (MH+).

Sources & evidence

ORD record: ord-608b3c95af1a4768ac2d02f52d5e67d8
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666834B2

Reaction notes

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