Sodium Hydroxide → HCID 86613241, compound

HRID 1660703Notes

Reaction equation

C[O:2][C:3](=[O:26])[CH2:4][C@H:5]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]([CH3:9])[CH3:8].[OH-].[Na+]>C1COCC1.CO>[C:14]([O:13][C:11]([NH:10][C@H:6]([CH:7]([CH3:9])[CH3:8])[C@@H:5]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:21])[CH2:4][C:3]([OH:26])=[O:2])=[O:12])([CH3:15])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 47 (500 mg, 1.28 mmol) in 25 mL of THF/MeOH (1:1), cooled to 0° C., 1N NaOH solution (25 mL) 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 48 was obtained as a colorless oil (1.76 g, 86%) and used directly in the next step. 1H-NMR (500 MHz, CDCl3): 0.06 (s, 6H), 0.84-0.95 (m, 15H), 1.43 (s, 9H), 2.01-2.11 (m, 1H), 2.53 (m, 1H), 2.64 (m, 1H), 3.53-3.58 (m, 1H), 4.10-4.14 (m, 1H), 3.65 (s, 3H), 4.17-4.19 (m, 1H), 4.51-4.54 and 6.29-6.31 (m, 1H).

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-b2c7b89849f84885ac2a7d457bc3799d
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030279B2

Reaction notes

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