Hydrochloric Acid → HCID 68605074, compound

HRID 2267602Notes

Reaction equation

HRID 2267602 reaction equation
C[O:2][C:3](=[O:19])[C@H:4]([CH2:17][OH:18])[NH:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=1.[OH-].[Li+].Cl>C1COCC1.[Cl-].[Na+].O>[F:14][C:12]1[CH:13]=[C:8]([CH2:7][C:6]([NH:5][C@H:4]([C:3]([OH:19])=[O:2])[CH2:17][OH:18])=[O:16])[CH:9]=[C:10]([F:15])[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68605042HCID 68605042, compound

Product 1

HCID 68605074HCID 68605074, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of N-[(3,5-difluorophenyl)acetyl]-L-serine methyl ester (4a) in THF (13 mL) was added 1M aqueous lithium hydroxide (13.2 mL) and the mixture stirred at RT for 40H. Brine (50 mL) was added, the aqueous layer made acidic to pH 1 with 1N hydrochloric acid (˜15 mL), and the aqueous layer extracted with 10% Methanol/CHCl3 (2×). The organic phase was collected, dried, filtered and the solvent removed in vacuo to afford the title compound (112 mg, 54%). This material was used without further purification. 1H NMR (300 MHz, d6-DMSO) δ3.57 (d, 2H), 3.7 (m, 1H), 4.27, (m, 1H), 5.03 (bs, 1H), 7.00 (d, 2H), 7.09 (t, 1H), 8.38, (d, 1H). 12.6, (bs, 1H). MS APCI, m/z=274 (M+1). LC/MS: 1.0 min.

Workup

  1. extractionthe aqueous layer extracted with 10% Methanol/CHCl3 (2×)
  2. customThe organic phase was collected
  3. customdried
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4331525844ed4724a57f3bd2caffe3c2
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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