(Diethylamino)sulfur trifluoride → HCID 131733203, compound

HRID 1527394Notes

Reaction equation

HRID 1527394 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([C:14]([CH3:22])([CH3:21])[O:15][SiH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])(O)[CH2:10][C@H:9]1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:39])CC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([C:14]([CH3:22])([CH3:21])[O:15][SiH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])([F:39])[CH2:10][C@H:9]1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 131733204HCID 131733204, compound

Product 1

HCID 131733203HCID 131733203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (5.20 g, 11.17 mmol) in CH2Cl2 (100 mL) at −78° C. was added DAST (2.21 mL, 16.75 mmol). The solution was stirred for 16 hours at RT then was washed with sat NaHCO3 (2×100 mL). The organic layer was dried with Na2SO4, filtered and concentrated. Purification by flash column chromatography on silica gel (c-hexane/EtOAc 9:1). MS (UPLC/MS): 468 [M+H]+, 512 [M+HCOO]−; tR (HPLC conditions f): 3.00 min.

Workup

  1. washthen was washed with sat NaHCO3 (2×100 mL)
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (c-hexane/EtOAc 9:1)
  6. custom3.00 min.

Sources & evidence

ORD record
ord-6cc7879c0af04c71b049bd5abc1e64ff
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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