2-Bromo-4-fluorobenzene-1-sulfonyl chloride → Methyl (S)-7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3,3a,4-tetrahydro-1 H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate

HRID 715949Notes

Reaction equation

HRID 715949 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:17]2[O:18][CH2:19][C@H:20]3[CH2:24][CH2:23][CH2:22][N:21]3[C:16]2=[CH:15][CH:14]=1)(=[O:11])=[O:10].NC1C(C(OC)=O)=C2OC[C@@H]3CCCN3C2=CC=1.BrC1C=C(F)C=CC=1S(Cl)(=O)=O>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:17]2[O:18][CH2:19][C@@H:20]3[CH2:24][CH2:23][CH2:22][N:21]3[C:16]2=[CH:15][CH:14]=1)(=[O:11])=[O:10]

Participants

4

Reactant 3

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chlorideHCID 71003749methyl (R)-7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylateHCID 86712112Methyl (S)-7-amino-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate2×

Product 1

HCID 71003669Methyl (S)-7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3,3a,4-tetrahydro-1 H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 2, starting from methyl (S)-7-amino-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate (Intermediate 13), and 2-bromo-4-fluorobenzenesulfonyl chloride.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9642fa5b2edf4f74bd04092d26708886
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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