Sulfuryl chloride → N-Benzyloxycarbonyl 2-chloro-4,5-dihydroxyphenylglycine

HRID 1788827Notes

Reaction equation

HRID 1788827 reaction equation
[CH2:1]([O:8][C:9]([N:11]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:23])[CH:17]=1)[CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:27])(=O)=O>C(O)(=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]([C:16]1[CH:17]=[C:18]([OH:23])[C:19]([OH:22])=[CH:20][C:21]=1[Cl:27])[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

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 54431662N-Benzyloxycarbonyl 3,4-dihydroxyphenylglycine

Product 1

HCID 54341029N-Benzyloxycarbonyl 2-chloro-4,5-dihydroxyphenylglycine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxycarbonyl 3,4-dihydroxyphenylglycine (0.79 g, 2.5 mmole) in acetic acid (10 ml) was treated with sulphuryl chloride (0.2 ml), stirred at room temperature for two hours then diluted with ethyl acetate (50 ml), washed with water (2×3 ml) and brine (20 ml), dried and evaporated to a gum which was crystallized from chloroform, 0.36 g, 41%, mp 141°-143°.

Workup

  1. washwashed with water (2×3 ml) and brine (20 ml)
  2. customdried
  3. customevaporated to a gum which
  4. customwas crystallized from chloroform, 0.36 g, 41%, mp 141°-143°

Sources & evidence

ORD record
ord-8be6c565ef5649d1915be6fdfbac7331
Source dataset
uspto-grants-1987_08
Patent number
US04684639

Reaction notes

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