Hydrochloric Acid → HCID 178499254, compound

HRID 1694489Notes

Reaction equation

HRID 1694489 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-88a0badd5bbd4894bb0a24ce0d55844d
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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