Triphenylphosphine → (s)-2-Benzyloxycarbonylamino-3-(6-chloro-purin-9-yl)-propionic acid tert-butyl ester

HRID 352387Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:42]([O:46][C:47](=[O:62])[C@H:48]([CH2:60]O)[NH:49][C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])([CH3:45])([CH3:44])[CH3:43]>C1COCC1>[C:42]([O:46][C:47](=[O:62])[C@@H:48]([NH:49][C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:60][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[Cl:1])([CH3:43])([CH3:44])[CH3:45]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 7.73 g (50 mmol) of 6-chloropurine in 350 ml of absolute THF were added 14.43 g (55 mmol) triphenylphosphine at −10 to 0° C. followed by 9.57 g (55 mmol) of diethyl azodicarboxylate and 14.8 g (50 mmol) of N-benzyloxycarbonyl-L-serine tert-butyl ester in 100 ml of absolute THF, and the mixture was stirred at 0° C. for 48 h. The solvent was evaporated, the residue was dissolved in EE/heptane (2:1), filtered and the solvent was removed in vacuo. The crude product was purified by flash chromatography on silica gel (EE/n-heptane (1:1) and DCM/EE (85:15)). Yield: 6.6 g.

Workup

customThe solvent was evaporated
dissolutionthe residue was dissolved in EE/heptane (2:1)
filtrationfiltered
customthe solvent was removed in vacuo
customThe crude product was purified by flash chromatography on silica gel (EE/n-heptane (1:1) and DCM/EE (85:15))

Sources & evidence

ORD record: ord-822b8fc58d8144c9805545109c5f6d27
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747016B1

Reaction notes

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