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

HRID 1729642Notes

Reaction equation

HRID 1729642 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-sulphonyloxymethyl)morpholine (18.1 g.) in methanol (100 ml.) was added a solution of (+)-toluene-p-sulphonylglutamic acid (16.0 g.) in methanol (50 ml.) and the mixture was allowed to crystallise during 12 hours. The mixture was filtered, the filtrate was put on one side, and the filtered solids (18.3 g.) were recrystallised from methanol (150 ml.) to obtain the (+)-toluene-p-sulphonylglutamic acid salt of (2S)-4-benzyl-2-(toluene-p-sulphonyloxymethyl)morpholine (14.0 g.), m.p. 184° C. This salt was stirred with a mixture of 2N sodium hydroxide and ether. The ether layer was separated, dried and the ether was distilled to leave optically pure (2S)-4-benzyl-2-(toluene-p-sulphonyloxymethyl)morpholine as an oil, from which was 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 was filtered
  3. customthe filtered solids (18.3 g.) were recrystallised from methanol (150 ml.)

Sources & evidence

ORD record
ord-12624340956a4b81a8029d7c052d1e5b
Source dataset
uspto-grants-1976_11
Patent number
US03989699

Reaction notes

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