Potassium Bromide → HCID 118354234, compound

HRID 525304Notes

Reaction equation

HRID 525304 reaction equation
[C:1]([O:5][C:6](=[O:31])[N:7]([C@H:9]([C:11](=[O:30])[NH:12][C@H:13]([C:17]([N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21][CH:20]1[CH2:28][OH:29])=[O:18])[CH:14]([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[K+].[Br-].[O-]Cl.[Na+]>C(Cl)Cl.CC1(C)N([O])C(C)(C)CCC1>[C:1]([O:5][C:6](=[O:31])[N:7]([C@H:9]([C:11](=[O:30])[NH:12][C@H:13]([C:17]([N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21][C@H:20]1[CH:28]=[O:29])=[O:18])[CH:14]([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 253877Potassium BromideHCID 23665760Sodium HypochloriteHCID 117869999HCID 117869999, compound

Product 1

HCID 118354234HCID 118354234, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To {(S)-1-[(S)-1-(2-hydroxymethyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (16.5 mg, 0.038 mmol) in DCM (0.4 mL) at 0° C. was added sequentially KBr (3.1 g, 0.027 mmol), TEMPO (0.3 mg) and 8% NaOCl solution (0.35 mL, 10 eq) and the reaction was stirred vigorously for 1 h. The reaction mixture was diluted with DCM and washed with water and brine and then concentrated in vacuo to give {(S)-1-[(S)-1-((S)-2-formyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (12 mg).

Workup

  1. washwashed with water and brine
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2322431d140f4d2bb5b99cf6c267d60e
Source dataset
uspto-grants-2016_05
Patent number
US09340573B2

Reaction notes

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