L-Phenylalanine → HCID 86739179, compound

HRID 2295520Notes

Reaction equation

HRID 2295520 reaction equation
[C:1]([S:9][CH2:10][CH2:11][C:12]([N:14]1[C@H:18](C(O)=O)[CH2:17][S:16][C@@H:15]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CC[O:33][CH2:32]C1.C(Cl)(=O)O[CH2:38][CH:39](C)C.[NH2:44][C@H:45]([C:53]([OH:55])=[O:54])[CH2:46]C1C=CC=CC=1.[CH2:56]1[CH2:60]O[CH2:58][CH2:57]1>C(N(CC)CC)C>[C:1]([S:9][CH2:10][CH2:11][C:12]([N:14]1[C@H:18]([C:32]([N:44]([C:56]2[CH:57]=[CH:58][CH:39]=[CH:38][CH:60]=2)[C@H:45]([C:53]([OH:55])=[O:54])[CH3:46])=[O:33])[CH2:17][S:16][C@@H:15]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6140L-PhenylalanineHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 12915689HCID 12915689, compound

Product 1

HCID 86739179HCID 86739179, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To the suspension of 2.09 g of (2R,4R)-3-(S-benzoyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid, 0.51 g of N-methylmorpholine and 0.68 g of isobutyl chlorocarbonate in THF, the solution of 1.65 g of L-phenylalanine and 1.0 g of triethylamine is added, and the mixture is treated in the same manner as Example 10. The resulting residue is purified by silica gel column chromatography to give 2.0 g (71%) of the titled compound.

Workup

  1. additionthe mixture is treated in the same manner as Example 10
  2. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8d76011a2a734b529a9d8a54eab1ce65
Source dataset
uspto-grants-1984_01
Patent number
US04425333

Reaction notes

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