Pyridine → HCID 178474822, compound

HRID 1919459Notes

Reaction equation

HRID 1919459 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:27])([CH3:26])[C@@H:14]([OH:25])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21](=[O:24])[CH2:22]O)=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2].[P:28](Cl)(OC1C=CC=CC=1)([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29].N1C=CC=CC=1.C(N(CC)CC)C>ClCCl>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:26])([CH3:27])[C@@H:14]([OH:25])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21](=[O:24])[CH2:22][PH:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 25225745HCID 25225745, compound

Product 1

HCID 178474822HCID 178474822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the general procedure for phosphorylation of Description 23, (2-hydroxyacetyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-hydroxy-butanoate (45) (40 mg, 0.10 mmol) dissolved in 2 mL of anhydrous dichloromethane (DCM) was reacted with 60 L (78 mg, 0.29 mmol) of diphenyl chlorophosphate [(PhO)2POCl] in the presence of pyridine (15.6 μL, 15.3 mg, 0.19 mmol) and triethylamine (TEA) (13.5 μL, 9.8 mg, 0.10 mmol). The reaction was monitored by TLC. After aqueous work-up, the crude title compound (53a) was obtained and used in the next step without purification. MS (ESI) m/z 646.05 (M+H)+, 668.02 (M+Na)+.

Sources & evidence

ORD record
ord-91a76f77c9f14878840d2cf2faa56b24
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

Loading…