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

HRID 437194Notes

Reaction equation

HRID 437194 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 twelve hours. The mixture is filtered and the residue (18.3 g.) is recrystallised 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 twelve hours
  2. filtrationThe mixture is filtered
  3. customthe residue (18.3 g.) is recrystallised from methanol (150 ml.)

Sources & evidence

ORD record
ord-d93aef91e34247688fbde80e4e80dda4
Source dataset
uspto-grants-1977_06
Patent number
US04029786

Reaction notes

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