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

HRID 2260002Notes

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-8efdff004dae4feeb04bfd6c3b6acfb1
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05475129

Reaction notes

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