Triethylamine → HCID 68283592, compound

HRID 1527418Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([F:16])[C@@H:13]([OH:17])[C@H:12]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([Si:32]([CH3:35])([CH3:34])Cl)([CH3:31])([CH3:30])[CH3:29].C(N(CC)CC)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([F:16])[C@@H:13]([O:17][Si:32]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:35])[CH3:34])[C@H:12]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (2S,3S,4S)-4-fluoro-3-hydroxy-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester (1.90 g, 5.09 mmol) in DMF (40 mL) were added tert-butyldimethylchlorosilane (0.844 g, 5.60 mmol), triethylamine (0.709 ml, 5.09 mmol) and DMAP (0.062 g, 0.509 mmol). The reaction mixture was stirred 25° C. for 1 week. Then quenched by addition of a saturated aqueous solution of NaHCO3. The layers were separated and the organic extract was dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1). MS (UPLC): 588.4 [M+H]+, 505.5 [M+NH4]+, 510.4 [M+Na]+; tR (HPLC conditions f): 2.90 min.

Workup

customThen quenched by addition of a saturated aqueous solution of NaHCO3
customThe layers were separated
extractionthe organic extract
dry with materialwas dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1)
custom2.90 min.

Sources & evidence

ORD record: ord-1ebada83f0a14c31be47c13f48a2ac7d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085555B2

Reaction notes

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