Triethylamine → Methyl 4-[bis(tert-butoxy)phosphorylhydroxymethyl]-N-(benzyloxycarbonyl)-D,L-phenylalaninate

HRID 258168Notes

Reaction equation

[C:1]([O:5][P:6]([CH:13]([OH:27])[C:14]1[CH:26]=[CH:25][C:17]([CH2:18][CH:19]([C:21]([O:23][CH3:24])=[O:22])[NH2:20])=[CH:16][CH:15]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.Cl[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]>C1COCC1.CCOCC>[C:9]([O:8][P:6]([CH:13]([OH:27])[C:14]1[CH:26]=[CH:25][C:17]([CH2:18][CH:19]([C:21]([O:23][CH3:24])=[O:22])[NH:20][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37])=[CH:16][CH:15]=1)([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])([CH3:10])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 8 (876 mg, 2.18 mmol) in THF (22 mL) at 0° C. was added NEt3 1.22 mL, 8.74 mmol), followed by benzyl chloroformate (0.34 mL, 2.40 mmol) dropwise via syringe. The reaction was stirred at 0° C. for 0.5 hours, then diluted with Et2O (20 mL) and quenched by dropwise addition of brine (1 mL). Additional brine (20 mL) was added and the organic phase separated and combined with an Et2O extract (2×20 mL) of the residual brine. The combined Et2O was dried (MgSO4), filtered and solvent removed by rotary evaporation under reduced pressure to yield crude 9 (1.03 g, 88%). Silica gel chromatography [EtOAc/hexanes (4:3)] provided pure 9 (621 mg, 53%).

Workup

customquenched by dropwise addition of brine (1 mL)
additionAdditional brine (20 mL) was added
customthe organic phase separated
extractionextract (2×20 mL) of the residual brine
dry with materialThe combined Et2O was dried (MgSO4)
filtrationfiltered
customsolvent removed by rotary evaporation under reduced pressure

Sources & evidence

ORD record: ord-df9b527ae6334d71b2da0aef43e5c06a
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05264607

Reaction notes

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