Methanol → HCID 743119, compound

HRID 411267Notes

Reaction equation

[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([N:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][C:12]([OH:14])=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:26]O>>[CH3:26][O:13][C:12](=[O:14])[CH2:11][N:10]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:21])=[CH:6][CH:5]=1)(=[O:9])=[O:8]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 362727HCID 362727, compound

Product 1

HCID 743119HCID 743119, compound

Procedure

N-(Toluene-4-sulfonyl)phenylglycine was esterified with thionyl chloride in methanol to give N-(toluene-4-sulfonyl)phenylglycine methyl ester. This was then taken up in dry acetone (50 mL) with iodomethane (1.1 eq, 1.88 mL) and K2CO3 (1.1 eq, 4.10 g). The solution was refluxed overnight. The solvent was evaporated under reduced pressure. EtOAc was added and the organic layer was washed with brine. The organic layer was dried over MgSO4. The solvent was evaporated under reduced pressure. The resulting ester was hydrolyzed using the procedure described in Method 6 to yield N-(Toluene-4-sulfonyl)-N-methylphenylglycine, which was coupled with L-phenylalanine ethyl ester using the procedure described in Method 3 to yield the title compound.

Sources & evidence

ORD record: ord-d526fd1294244e91823b35d52ba5adfd
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559127B1

Reaction notes

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