Hydrochloric Acid → HCID 178499257, compound

HRID 1675534Notes

Reaction equation

HRID 1675534 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:27])=[CH:8][C:9]=1[N:10]([C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])[CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)=[O:4].[BH4-].[Na+].Cl>CO.CCOC(C)=O.CCCCCC>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:27])=[CH:8][C:9]=1[N:10]([C@H:11]1[CH2:12][CH2:13][C@H:14]([OH:17])[CH2:15][CH2:16]1)[C:18]([C@H:20]1[CH2:21][CH2:22][C@H:23]([CH3:26])[CH2:24][CH2:25]1)=[O:19])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178499251HCID 178499251, compound

Product 1

HCID 178499257HCID 178499257, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

To a cold (0° C.) solution of 5-bromo-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (5.9 g, 12.9 mmol) in 50 mL of MeOH under a N2 atmosphere, NaBH4 (250 mg, 6.4 mmol) is added portion wise (approx. 30 min). After the addition is completed and checked for reaction completion by TLC (hexane:EtOAc 1:1), 10 mL of HCl 2% is added and stirred for 15 min. The reaction mixture is concentrated under vacuum to dryness. The reaction mixture is recuperated with water (25 mL) and extracted with EtOAC. The organic phases are combined and dried over MgSO4 and concentrated to dryness. The residue is purified by silica get column chromatography using EtOAc:hexane (1:1) as eluent to obtain 5-bromo-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexane-carbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (4.5 g, 77% yield) as a solid.

Workup

  1. additionAfter the addition
  2. additionis added
  3. concentrationThe reaction mixture is concentrated under vacuum to dryness
  4. extractionextracted with EtOAC
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by silica
  8. customget column chromatography

Sources & evidence

ORD record
ord-44ef727e45c141d3ad95fe64c77e729e
Source dataset
uspto-grants-2011_08
Patent number
US08003685B2

Reaction notes

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