Hydrochloric Acid → HCID 178499296, compound

HRID 1694440Notes

Reaction equation

HRID 1694440 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH2:32][CH2:31][C:30]([CH3:34])([CH3:33])[CH2:29][CH:28]=2)=[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>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH2:32][CH2:31][C:30]([CH3:33])([CH3:34])[CH2:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)[C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])=[O:4].[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH2:32][CH2:31][C:30]([CH3:33])([CH3:34])[CH2:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([OH:17])[CH2:13][CH2:12]1)[C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178499289HCID 178499289, compound

Product 2

HCID 178499296HCID 178499296, compoundHCID 178499297HCID 178499297, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(4,4-dimethyl-cyclohex-1-enyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (13.3 g, previous reaction) in 195 mL of MeOH at 0° C. was added NaBH4 (450 mg, 11.9 mmol) portion wise. The reaction mixture was stirred for 1 hour at 0° C. After completion of the reaction, HCl (1N) was slowly added. The mixture was evaporated to dryness and the residue partitioned in EtOAc and water. The water phase was extracted (3×) and the combined organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by silica gel column chromatography using (30:70) EtOAc:hexane as eluent to obtain 5-(4,4-dimethyl-cyclohex-1-enyl)-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (5155 mg) as a solid and 5-(4,4-dimethyl-cyclohex-1-enyl)-3-[(cis-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (789 mg) as a solid. The overall yield for steps III, IV and V was 51%.

Workup

  1. additionwas slowly added
  2. customThe mixture was evaporated to dryness
  3. customthe residue partitioned in EtOAc
  4. extractionThe water phase was extracted (3×)
  5. washthe combined organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8a09a3604130477b88ed8357e3a203eb
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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