Sodium Sulfate → HCID 86709692, compound

HRID 2285400Notes

Reaction equation

HRID 2285400 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[C@@H:10]([N:13]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[F:36][C:37]([F:45])(S(F)(=O)=O)C(O)=O>C(#N)C>[CH2:1]([O:8][C:9](=[O:28])[C@@H:10]([N:13]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:11][O:12][CH:37]([F:45])[F:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 12835763HCID 12835763, compound

Product 1

HCID 86709692HCID 86709692, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A solution of (S)-2-dibenzylamino-3-hydroxy-propionic acid benzyl ester (4.9 g, 13.1 mmol) in acetonitrile (50 mL) was treated with anhydrous sodium sulfate (466 mg, 3.28 mmol) and warmed to 40° C. Difluoro(fluorosulfonyl)acetic acid (1.62 mL, 19.7 mmol) was then added over 90 minutes using a syringe pump. After the end of addition, the volatiles were removed in vacuo and the residue was purified by silica gel chromatography using a gradient of iso-hexanes/ethyl acetate 1:0 to 95:5 to provide (760 mg, 14%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 3.64 (d, J=13.8 Hz, 2H), 3.73 (app t, J=6.5 Hz, 1H), 3.87 (d, J=13.8 Hz, 2H), 4.09 (dd, J=10.3, 6.2 Hz, 1H), 4.22 (dd, J=10.3, 6.9 Hz, 1H), 5.21, 5.32 (ABq, JAB=12.3 Hz, 2H), 6.16 (t, J=74.7 Hz, 1H), 7.21-7.37 (m, 10H), 7.38-7.47 (m, 5H). LCMS (m/z) 426.1 [M+H], Tr=3.76 min.

Workup

  1. additionAfter the end of addition
  2. customthe volatiles were removed in vacuo
  3. customthe residue was purified by silica gel chromatography
  4. customto provide (760 mg, 14%) as a pale yellow oil
  5. customLCMS (m/z) 426.1 [M+H], Tr=3.76 min.

Sources & evidence

ORD record
ord-3d76ddf52c7042b690271f821446303e
Source dataset
uspto-grants-2015_09
Patent number
US09145441B2

Reaction notes

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