Potassium Carbonate → HCID 67373441, compound

HRID 1805916Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].C([O:10][C:11]1[C:20]([CH3:21])=[CH:19][C:18]([CH2:22][CH2:23][CH2:24][O:25][P:26]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14])(=O)C>CO>[CH2:37]([O:36][P:26]([O:25][CH2:24][CH2:23][CH2:22][C:18]1[CH:19]=[C:20]([CH3:21])[C:11]([OH:10])=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

Conditions

Temperature: 25 °C

Procedure

K2CO3 (108 mg, 0.784 mmol) was added to a stirred solution of methyl 2-(acetyloxy)-5-(3-{[bis(benzyloxy)phosphoryl]oxy}propyl)-3-methylbenzoate (206.3 mg, 0.392 mmol) in MeOH (26.1 mL) at 25° C. The reaction was stirred at 25° C. for 1 h. The reaction mixture was concentrated in vacuo and the resulting residue was partitioned between water (20 mL) and EtOAc (20 mL). The aqueous layer was separated and extracted with EtOAc (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford methyl 5-(3-{[bis(benzyloxy)phosphoryl]oxy}propyl)-2-hydroxy-3-methylbenzoate, as a colorless oil. LCMS calc.=485.2; found=485.0 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe resulting residue was partitioned between water (20 mL) and EtOAc (20 mL)
customThe aqueous layer was separated
extractionextracted with EtOAc (2×20 mL)
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-803ef880aae1438c9bb250b84e94b32d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354454B2

Reaction notes

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