Acetic Anhydride → N-Benzyloxycarbonyl 2-chloro-4,5-diacetoxyphenylglycine

HRID 1788828Notes

Reaction equation

HRID 1788828 reaction equation
[CH2:1]([O:8][C:9]([N:11]([C:16]1[CH:21]=[C:20]([OH:22])[C:19]([OH:23])=[CH:18][C:17]=1[Cl:24])[CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:31](OC(=O)C)(=[O:33])[CH3:32].C1C[O:41][CH2:40][CH2:39]1>O>[CH2:1]([O:8][C:9]([N:11]([C:16]1[CH:21]=[C:20]([O:22][C:31](=[O:33])[CH3:32])[C:19]([O:23][C:40](=[O:41])[CH3:39])=[CH:18][C:17]=1[Cl:24])[CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7918Acetic Anhydride2×HCID 8028TetrahydrofuranHCID 10340Sodium Carbonate2×HCID 54341029N-Benzyloxycarbonyl 2-chloro-4,5-dihydroxyphenylglycine

Product 1

HCID 53660034N-Benzyloxycarbonyl 2-chloro-4,5-diacetoxyphenylglycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Benzyloxycarbonyl 2-chloro-4,5-dihydroxyphenylglycine (1.76 g, 5 mmole) in water (30 ml) and THF (20 ml) was adjusted to pH 7.5 with saturated sodium carbonate solution. Acetic anhydride (1.2 ml) was added and pH 6.5 maintained with saturated sodium carbonate solution, after 15 minutes and again after a further 15 minutes more acetic anhydride (0.6 ml) was added. After another 15 minutes the solution was washed with ether (2×25 ml), acidified to pH 2.5 and extracted with ethyl acetate (3×30 ml). The extracts were washed with water (2×25 ml) and brine (20 ml) dried and evaporated to a foam, 1.87 g 86%, δ[(CD3)2CO] 2.20(6H, s, 2×OCOCH3), 5.03(2H, s, OCH2), 5.80(1H, d, J8 Hz, CHNH), 7.12(1H, d, J8 Hz, CHNH), 7.23(5H, s, Ph), 7.33 and 7.35(2H, 2×s, Ar), 9.57(1H, s, CO2H).

Workup

  1. additionwas added
  2. washAfter another 15 minutes the solution was washed with ether (2×25 ml)
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. washThe extracts were washed with water (2×25 ml) and brine (20 ml)
  5. customdried
  6. customevaporated to a foam, 1.87 g 86%, δ[(CD3)2CO] 2.20(6H

Sources & evidence

ORD record
ord-f891e300ccd949b285d97d069a945d6c
Source dataset
uspto-grants-1987_08
Patent number
US04684639

Reaction notes

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