Methanol → HCID 67073707, compound

HRID 454984Notes

Reaction equation

HRID 454984 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[O:12][CH3:13])[CH2:3][OH:4].[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(O)=O.[Na+].CO>C1COCC1.O.C(Cl)Cl>[CH2:14]([O:21][C:22](=[O:23])[NH:1][C@H:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[O:12][CH3:13])[CH2:3][OH:4])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 66513497HCID 66513497, compound

Product 1

HCID 67073707HCID 67073707, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 4-((R)-1-amino-2-hydroxy-ethyl)-3-methoxy-phenol (542 mg, 2.96 mmol), benzylchloroformate (634 uL, 4.44 mmol) and NaHCO3 (497 mg, 5.92 mmol) in THF/H2O (15/10 mL) was stirred at rt for overnight. After aqueous work up, the titled compound (736.3 mg, 79%) was obtained by flash column (5-7% MeOH in DCM).

Sources & evidence

ORD record
ord-84e357b44cea4e2a8b53ea7e61eec5bc
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Reaction notes

Loading…