N-[(4-Methylphenyl)sulfonyl]-L-glutamic acid → HCID 12297768, compound

HRID 1283113Notes

Reaction equation

HRID 1283113 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(N[C@H](C(O)=O)CCC(O)=O)(=O)=O)=CC=1>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][O:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2063452N-[(4-Methylphenyl)sulfonyl]-L-glutamic acidHCID 122977674-Benzyl-2-toluene-p-sulphonyloxymethylmorpholine

Product 1

HCID 12297768HCID 12297768, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4-benzyl-2-(toluene-p-sulphonyloxy)methylmorpholine (18.1 g.) in methanol (100 ml.) is added a solution of (+)-toluene-p-sulphonylglutamic acid (16.0 g.) in methanol (50 ml.) and the mixture is allowed to crystallise during 12 hours. The mixture is filtered and the residue (18.3 g.) is recrystallized from methanol (150 ml.) to obtain the (+)-toluene-p-sulphonylglutamic acid salt of (2S)-4-benzyl-2-(toluene-p-sulphonyloxy)methylmorpholine (14.0 g.), m.p. 184°C. This salt is stirred with a mixture of 2N sodium hydroxide and ether. The ether layer is separated, dried and the ether is distilled to leave optically pure (2S)-4-benzyl-2-(toluene-p-sulphonyloxy)methylmorpholine as an oil from which is prepared the hydrochloride, m.p. 150°C., [α]D25 + 19.4° (c,5 in methanol).

Workup

  1. customto crystallise during 12 hours
  2. filtrationThe mixture is filtered
  3. customthe residue (18.3 g.) is recrystallized from methanol (150 ml.)

Sources & evidence

ORD record
ord-f395e2d2ed8a42b6b9cd7c5f35c8a944
Source dataset
uspto-grants-1976_08
Patent number
US03974158

Reaction notes

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