methyl (1aRS,7bSR)-5-[N-(2-bromo-4-fluorobenzenesulfonyl)-N-(methoxycarbonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate → Methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-4-hydroxybut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927959Notes

Reaction equation

HRID 927959 reaction equation
[CH3:1][O:2][C:3]([N:5]([C:20]1[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]2[C:23]([CH:24]3[CH2:34][CH:25]3[CH2:26][O:27]2)=[CH:22][CH:21]=1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1/[CH:16]=[CH:17]\[CH2:18]O)(=[O:8])=[O:7])=[O:4].BrC1C=C(F)C=CC=1S(N(C1C(C(OC)=O)=C2C(C3CC3CO2)=CC=1)[C:47](OC)=[O:48])(=O)=O>>[CH3:1][O:2][C:3]([N:5]([C:20]1[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]2[C:23]([CH:24]3[CH2:34][CH:25]3[CH2:26][O:27]2)=[CH:22][CH:21]=1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1/[CH:16]=[CH:17]\[CH2:18][CH2:47][OH:48])(=[O:7])=[O:8])=[O:4]

Participants

3

Reactant 2

HCID 77979724methyl (1aRS,7bSR)-5-[N-(2-bromo-4-fluorobenzenesulfonyl)-N-(methoxycarbonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate2×HCID 86713304methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-3-hydroxyprop-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

Product 1

HCID 86713307Methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-4-hydroxybut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 64, starting from methyl (1aRS,7bSR)-5-[N-(2-bromo-4-fluorobenzenesulfonyl)-N-(methoxycarbonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (Intermediate 65) and (Z)-4-tributylstannanylprop-3-en-1-ol (prepared according to Miura et al, Organic Letters, 2005, 7(3) 503).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5c4a1935611640438e189054178385de
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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