L-Leucine → HCID 13316869, compound

HRID 2295514Notes

Reaction equation

HRID 2295514 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][CH:42]([CH3:44])[CH3:43]>C1COCC1.C(N(CC)CC)C>[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][CH:42]([CH3:44])[CH3:43])=[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

7

Reactant 4

HCID 6106L-LeucineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 13316857HCID 13316857, compound

Product 1

HCID 13316869HCID 13316869, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

The suspension of mixed anhydride in THF is prepared by using 1.78 g of (2R,4R)-3-(S-acetyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid, 0.51 g of N-methylmorpholine and 0.68 g of isobutyl chlorocarbonate. To the suspension the aqueous solution of 1.31 g of L-leucine and 1.0 g of triethylamine is added, and treated in the same manner as Example 1 to give 1.8 g (77%) of the titled compound.

Workup

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

Sources & evidence

ORD record
ord-356b968756d84661b6dfa31ec3763f21
Source dataset
uspto-grants-1984_01
Patent number
US04425333

Reaction notes

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