Sodium Hydroxide → HCID 11270901, compound
Reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C@H:5]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[C@H:6]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH:7]([CH3:9])[CH3:8].[OH-].[Na+]>C1COCC1.CO>[CH2:14]([O:13][C:11]([NH:10][C@H:6]([CH:7]([CH3:9])[CH3:8])[C@@H:5]([O:21][Si:22]([CH:23]([CH3:25])[CH3:24])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH2:4][C:3]([OH:32])=[O:2])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 13 (2.2 g, 4.7 mmol) in 50 mL of THF/MeOH (1:1), cooled to 0° C., 1N NaOH solution (55 mL, 32 mmol) was added. The reaction was stirred at 0° C. for 2 h and then overnight at rt. The reaction mixture was concentrated and diluted with H2O (20 mL), cooled to 0° C., acidified to pH 2 with 1N KHSO4 solution and extracted with EtOAc (3×20 mL). The combined organic layers were washed with NaCl (50 mL, sat), dried (Na2SO4), filtered and evaporated. The resulting acid 14 was obtained as a colorless oil (1.76 g, 86%) and used directly in the next step. 1H-NMR (500 MHz, CDCl3): 0.86 (m, 3H), 0.95 (d, J=6.7 Hz, 3H), 1.04-1.14 (m, 21H), 1.90-2.00 (m, 1H), 2.52-2.72 (m, 2H), 3.60-3.62 (m, 1H), 4.28-4.36 (m, 1H), 5.02 (d, J=10.4 Hz, 1H), 5.07-5.13 (m, 3H), 7.25-7.35 (m, 5H).
Workup
- customovernight
- customat rt
- concentrationThe reaction mixture was concentrated
- additiondiluted with H2O (20 mL)
- temperaturecooled to 0° C.
- extractionextracted with EtOAc (3×20 mL)
- washThe combined organic layers were washed with NaCl (50 mL, sat)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-61142f32c8f749eaa5d6fef7f426564f
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030279B2
Reaction notes
Loading…