Trityl chloride → HCID 71502325, compound

HRID 2201274Notes

Reaction equation

[NH2:1][C@@H:2]([C:5]([OH:7])=O)[CH2:3][SH:4].B.O1CCCC1.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[NH2:1][C@H:2]([CH2:3][S:4][C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:5][OH:7]

Participants

Conditions

Temperature: 0 °C

Procedure

D-Cysteine (2.36 g, 19.48 mmol) was suspended in THF (40 mL) and cooled to 0° C. Borane-tetrahydrofuran complex (1 M in THF, 78 mL, 78 mmol) was added over 20 mins and the mixture was stirred at RT for 6 hours. The reaction was quenched with DMF (7 mL) and stirred for 25 mins. Trityl chloride (5.97 g, 21.43 mmol) was added and the mixture stirred for a further 16 hours. The reaction mixture was evaporated under vacuum. The residue was partitioned between DCM and water and the phases separated. The organic phase was passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 50% EtOAc/hexane, EtOAc, 10% MeOH/EtOAc and 20% MeOH/EtOAc gave the title compound.

Workup

customThe reaction was quenched with DMF (7 mL)
stirringstirred for 25 mins
stirringthe mixture stirred for a further 16 hours
customThe reaction mixture was evaporated under vacuum
customThe residue was partitioned between DCM and water
customthe phases separated
customevaporated under vacuum
customPurification by chromatography on silica
washeluting with 50% EtOAc/hexane, EtOAc, 10% MeOH/EtOAc and 20% MeOH/EtOAc

Sources & evidence

ORD record: ord-fc3622fb97194fdd96ae364d9e516613
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359381B2

Reaction notes

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