Methanol → HCID 11353239, compound

HRID 900356Notes

Reaction equation

HRID 900356 reaction equation
C[O:2][C:3](=[O:40])[CH:4]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:15]=2)=[CH:10][CH:9]=1.CO.[OH-].[K+]>O1CCCC1.O>[C:36]([O:35][C:33]([NH:32][CH:4]([CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[C:16]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:15]=2)=[CH:10][CH:9]=1)[C:3]([OH:40])=[O:2])=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

6

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 68818602HCID 68818602, compound

Product 1

HCID 11353239HCID 11353239, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-tert-Butoxy carbonylamino-3-[4-(4,6-diphenylpyrimidin-2-yl)-benzylsulfanyl]-propionic acid methyl ester, 0.18 g (0.32 mmol) in 10 mL of tetrahydrofuran and 5 mL of methanol was added 1.62 mL of 1.0M aq. KOH. The solution was stirred for 1 h at room temperature. The solution was diluted with 10 mL of water and acidified to pH 1-2. The aqueous was extracted with 3×30 mL portions of diethyl ether. The organic layers were combined, washed with sat. aq. NaHCO3, sat. aq. NaCl, dried (MgSO4). The solution was concentrated to the desired product in 0.10 g (57%) as an off-white solid. MP 250° C. decomp, Rf=0.09 (100% Ethyl Acetate); 1H NMR (DMSO-d6) 8.57 (d, 2H, J=9.3), 8.52-8.46b (m, 5H), 7.60-7.58 (m, 6H), 7.51 (d, 2H, J=9.3), 4.11 (m, 1H), 3.86 (s, 3H), 2.81 (dd, 1H, J=14.8, 5.0 Hz), 2.67 (dd, 1H, J=15.3, 10.3), 1.39 (s, 9H). LCMS m/z calcd for C31H31N3O4S: 541.2, found 542.6(M+1)

Workup

  1. extractionThe aqueous was extracted with 3×30 mL portions of diethyl ether
  2. washwashed with sat. aq. NaHCO3, sat. aq. NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationThe solution was concentrated to the desired product in 0.10 g (57%) as an off-white solid

Sources & evidence

ORD record
ord-de62d915fc4b4ee78b319de9e29feca4
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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