Sodium borohydride → HCID 71006901, compound

HRID 403355Notes

Reaction equation

HRID 403355 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:20][CH2:19][C:18](=[O:21])[C:14]2[N:15]=[CH:16][S:17][C:13]=2[C@H:12]1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>CO>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:20][CH2:19][C@@H:18]([OH:21])[C:14]2[N:15]=[CH:16][S:17][C:13]=2[C@H:12]1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71006902HCID 71006902, compound

Product 1

HCID 71006901HCID 71006901, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (9.93 mg, 0.262 mmol) was added to a methanol (5 mL) solution of tert-butyl (7S,8S)-7-(2,3-difluorophenyl)-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-8-ylcarbamate (34.5 mg, 0.087 mmol) at rt. The reaction was stirred for 0.5 h. The solvent was removed under vacuum and the product was purified by prep TLC developed with ethyl acetate in hexane (50%). There were two bands collected. The less polar was the desired product (20.1 mg. 58%): LCMS: M+H=397.24; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.57 (1H, s), 7.03-7.09 (3H, m), 5.16-5.23 (1H, m), 4.94-5.00 (1H, m), 4.85-4.91 (1H, m), 4.26 (1H, s), 3.28-3.36 (1H, m), 2.19-2.36 (3H, m), 1.64-1.69 (1H, m), 1.26-1.29 (8H, m).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe product was purified by prep TLC
  3. customcollected

Sources & evidence

ORD record
ord-9ea76cc915d14893ae1c05b736cca4fb
Source dataset
uspto-grants-2014_06
Patent number
US08748429B2

Reaction notes

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