Hydrochloric Acid → (-)-alpha-Amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid hydrochloride

HRID 903819Notes

Reaction equation

HRID 903819 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[ClH:13].[CH2:14]=O>CO>[ClH:13].[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:14][Cl:13])[CH:7]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 921434-Hydroxyphenylglycine

Product 1

HCID 70578051(-)-alpha-Amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (-)-α-amino-4-hydroxybenzeneacetic acid (100 g, 0.6 mole) in a minimum amount of concentrated hydrochloric acid at 35°-40° C. is added 50 ml of aqueous formaldehyde (35-37%) (0.6 mole). The addition of hydrogen chloride gas is begun. After 5-10 minutes, a solid begins to precipitate. Stirring is continued for 30 minutes, and the solid is then collected. The crude product is washed with ether and with acetone. A second crop is obtained from the filtrate after standing at room temperature overnight. Total yield is 102 g (67%) m.p. >300° C., [α]D18 =-134° (c 4.75, CH3OH) NMR (DMSO--D6) ppm (δ) 4.68 (s,2), 4.9 (broad s,1), 6.9-7.6 (superimposed q and s,3).

Workup

  1. customto precipitate
  2. waitis continued for 30 minutes
  3. customthe solid is then collected
  4. washThe crude product is washed with ether and with acetone
  5. customA second crop is obtained from the filtrate
  6. waitafter standing at room temperature overnight

Sources & evidence

ORD record
ord-5c3b64b3574749f2a10fdc0ac43328c6
Source dataset
uspto-grants-1980_10
Patent number
US04229363

Reaction notes

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