Methyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate → (1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate

HRID 926007Notes

Reaction equation

HRID 926007 reaction equation
[Si:1]([O:18][C@H:19]1[CH2:24][C@@H:23]([C:25](O)=[O:26])[C@H:22]([C:28](=[O:37])[N:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])[CH3:30])[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([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.[NH2:38][C@:39]1([C:44]([O:46][CH3:47])=[O:45])[CH2:41][C@H:40]1[CH:42]=[CH2:43].[Si](O[C@H]1C[C@@H](C(OC(C)(C)C)=O)[C@H](C(=O)N(CCCCC=C)C)CC1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>>[Si:1]([O:18][C@H:19]1[CH2:24][C@@H:23]([C:25]([NH:38][C@:39]2([C:44]([O:46][CH3:47])=[O:45])[CH2:41][C@H:40]2[CH:42]=[CH2:43])=[O:26])[C@H:22]([C:28](=[O:37])[N:29]([CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])[CH3:30])[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([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

Participants

4

Reactant 3

HCID 11355820Methyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylateHCID 58282725(1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylic acidHCID 58282736(1R,2R,5R)-tert-butyl 5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylate

Product 1

HCID 67213840(1R,2S)-methyl 1-((1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxamido)-2-vinylcyclopropanecarboxylate

Procedure

Compound 41 was synthesized from compound 40 and (1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate as described for compound 39 to yield compound 41 as a yellow oil in 76% yield. MS (ESI, EI+): m/z=645 (MH+)

Sources & evidence

ORD record
ord-4186aa642296497c85ddb637b70c8934
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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