Dicyclohexylcarbodiimide → benzotriazol-1-yl (2Z)-2-butoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate
Reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][CH2:33][CH2:34][CH3:35])/[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:37]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[N:38]1.C1(N=C=NC2CCCCC2)CCCCC1.N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC3N(NC(=O)C)N=NN=3)CS[C@H]12>O1CCCC1>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][CH2:33][CH2:34][CH3:35])/[C:27]([O:29][N:37]2[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[N:39]=[N:38]2)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-n-butoxyiminoacetic acid (1.6 g, 3.29 mmol) and 1-hydroxybenzotriazole (0.49 g, 3.62 mmol) in tetrahydrofuran (16 ml) was added N,N'-dicyclohexylcarbodiimide (0.75 g, 3.62 mmol) and the mixture was stirred at room temperature. Then the mixture was treated in a manner similar to that descirbed in Example 6, (b) to give colorless needles of 1-benzotriazolyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-n-butoxyiminoacetate (1.50 g, 75.7%), mp 100°-102° C.
Workup
- additionThen the mixture was treated in a manner similar to
Sources & evidence
- ORD record
- ord-8000c2193f8d42a48c93981340d0bcc8
- Source dataset
- uspto-grants-1986_03
- Patent number
- US04576938
Reaction notes
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