Hydrochloric Acid → HCID 178499254, compound

HRID 1190040Notes

Reaction equation

HRID 1190040 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:28])=[CH:8][C:9]=1[N:10]([CH:20]1[CH2:25][O:24]C(C)(C)[O:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:28])=[CH:8][C:9]=1[N:10]([CH:20]([CH2:25][OH:24])[CH2:21][OH:22])[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178499252HCID 178499252, compound

Product 1

HCID 178499254HCID 178499254, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-bromo-3-[(2,2-dimethyl-[1,3]dioxan-5-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (35 mg) contaminated with a small impurity in THF (1.1 mL) and 3N HCl (0.75 mL) was stirred at room temperature for 16 h. It was neutralized with solid NaHCO3 and evaporated down to dryness. The residue was triturated with ethyl acetate (3×8 mL). The ethyl acetate extracts were combined, evaporated and chromatographed over silica gel (hexane:EtOAc—1:1) yielding pure 5-bromo-3-[(2-hydroxy-1-hydroxymethyl-ethyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (18 mg; 7.2% in two steps).

Workup

  1. customevaporated down to dryness
  2. customThe residue was triturated with ethyl acetate (3×8 mL)
  3. customevaporated
  4. customchromatographed over silica gel (hexane:EtOAc—1:1)

Sources & evidence

ORD record
ord-0ea9525a86e54397af65bd48dfb1b8fb
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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