Sulfuric acid magnesium salt (1:1) → HCID 58291881, compound

HRID 1944763Notes

Reaction equation

HRID 1944763 reaction equation
C([O:3][C:4]([C:6]1([CH2:27][CH:28]=O)[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=O)C.[C:30]1([C@H:36]([NH2:38])[CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[O-]S([O-])(=O)=O.[Mg+2].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[O:3]=[C:4]1[C:6]2([CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)(=[O:14])=[O:15])[CH2:8][CH2:7]2)[CH2:27][CH2:28][N:38]1[C@@H:36]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:37]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 6431891-Phenethylamine, (+)-HCID 5049666Sodium triacetoxyborohydrideHCID 58292109HCID 58292109, compound2×

Product 1

HCID 58291881HCID 58291881, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

1-(2-oxo-ethyl)-4-(4-pyrazol-1-yl-benzenesulfonylamino)-cyclohexanecarboxylic acid ethyl ester (Intermediate 114, 40 mg, 0.095 mmol) and (R)-1-phenylethanamine (0.036 ml, 0.286 mmol) were dissolved in DCE (2 ml). MgSO4 was added (20-30 mg) followed by NaBH(OAc)3 (60.6 mg, 0.286 mmol). The reaction mixture was stirred overnight at room tempereature, then further DCE was added, and the reaction mixture was heated at 50° C. overnight. The reaction mixture was concentrated in vacuo, and the crude material taken up in DCM, and washed with water (×2). The organic layer was concentrated in vacuo, and the resultan crude oil was purified via normal phase chromatography using biotage SP1, with 25+S column, using a calculated gradient from TLC of 50% EtOAc in heptane to yield the title compound as a white solid (29 mg, 64%) as a mixture of 95% “trans” (as shown above): 5% “cis”. MS MH+ 479.1

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with water (×2)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe resultan crude oil was purified via normal phase chromatography

Sources & evidence

ORD record
ord-aa0e52cdd88d4e3ab5f12a54d51548dd
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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