Benzyl Alcohol → HCID 86748614, compound

HRID 651202Notes

Reaction equation

HRID 651202 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.O.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.[CH2:24](O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([C@@](C(O)=O)(CC(N(CCCl)CCCl)(C1C=CC=C(C)C=1)C(=O)N)NC(OC1C=CC=CC=1)=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:13]1([CH3:23])[CH:14]=[CH:15][C:16]([S:19]([OH:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1.[CH2:24]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 571807(3-Aminophenyl)acetic acidHCID 86752016alpha-benzyl 4-[N,N-bis(2-chloroethyl)-amino]phenoxycarbonyl-gamma-(3-methylphenyl)-L-glutamine

Product 1

HCID 86748614HCID 86748614, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

3-amino-phenylacetic acid benzyl ester p-toluene sulphonic acid was prepared by adding 3-aminophenylacetic acid (10 g) and p-toluene sulphonic acid monohydrate (13.2 g) to benzyl alcohol (27.2 ml) in toluene (30 ml). The mixture was heated under reflux and the water formed collected in a Dean-Stark receiver. When all the water had been distilled off the mixture was allowed to cool to 25° C. before diluting with diethyl ether and placing in an ice-bath for 1 hr. The crystalline p-toluene sulphonate was filtered off and dried in a dissicator (23.5 g) NMR δ 2.31(s)3H, 3.82(s)2H, 5.11(s)2H, 7.11(d)2H, 7.25-7.45(m)8H, 7.52(d)2H.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customcollected in a Dean-Stark receiver
  4. distillationWhen all the water had been distilled off the mixture
  5. additionbefore diluting with diethyl ether
  6. filtrationThe crystalline p-toluene sulphonate was filtered off
  7. customdried in a dissicator (23.5 g) NMR δ 2.31(s)3H, 3.82(s)2H, 5.11(s)2H, 7.11(d)2H, 7.25-7.45(m)8H, 7.52(d)2H

Sources & evidence

ORD record
ord-39c1dfe6c3664335ba8d574c2856116d
Source dataset
uspto-grants-2001_08
Patent number
US06277880B1

Reaction notes

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