Trityl chloride → N-trityl-t-butyldimethylsilyloxy serine methyl ester

HRID 863849Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:14][OH:15])[NH:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C(N(C(C)C)CC)(C)C.[C:26](Cl)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:14][OH:15])[N:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:8])[CH3:9])[C:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To t-butyldimethylsilyloxyserine methyl ester (27.5 g; 0.118 mol) dissolved in CH2Cl2 (125 ml) and diisopropylethylamine (25 ml; 0.14 mol) and cooled to 0° C. is added tritylchloride (33 g; 0.118 mol) portionwise over 2 minutes. The reaction is stirred for 4 hours at 25° C., diluted with CH2Cl2 and washed with H2O 3×. The organic phase is dried (MgSO4) and concentrated to dryness to give N-trityl-t-butyldimethylsilyloxy serine methyl ester as a tan solid which is used directly next Step C.

Workup

washwashed with H2O 3×
dry with materialThe organic phase is dried (MgSO4)
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-5a8a242c4f9d4c0cad5337e86a54d66f
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05561143

Reaction notes

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