L-Methionine → HCID 13316871, compound

HRID 2295515Notes

Reaction equation

HRID 2295515 reaction equation
[C:1]([S:4][CH2:5][CH2:6][C:7]([N:9]1[C@H:13]([C:14]([OH:16])=O)[CH2:12][S:11][C@@H:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:8])(=[O:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.[NH2:39][C@H:40]([C:45]([OH:47])=[O:46])[CH2:41][CH2:42][S:43][CH3:44]>C1COCC1>[C:1]([S:4][CH2:5][CH2:6][C:7]([N:9]1[C@H:13]([C:14]([NH:39][C@H:40]([C:45]([OH:47])=[O:46])[CH2:41][CH2:42][S:43][CH3:44])=[O:16])[CH2:12][S:11][C@@H:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6137L-MethionineHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 13316857HCID 13316857, compound

Product 1

HCID 13316871HCID 13316871, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The suspension of mixed anhydride in THF is prepared by using 5.3 g of (2R,4R)-3-(S-acetyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid, 1.5 g of N-methylmorpholine and 2.0 g of isobutyl chlorocarbonate. To the suspension the aqueous solution of 4.5 g of L-methionine and 3.0 g of N-methylmorpholine is added, and treated in the same manner as Example 1 to give 1.6 g (66%) of the titled compound.

Workup

  1. customis prepared
  2. additiontreated in the same manner as Example 1

Sources & evidence

ORD record
ord-15b4392de585466a8a1c07755f14692a
Source dataset
uspto-grants-1984_01
Patent number
US04425333

Reaction notes

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