4-Methylmorpholine → HCID 13316885, compound

HRID 2295516Notes

Reaction equation

HRID 2295516 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.[NH:39]1[CH2:46][CH2:45][CH2:44][C@H:40]1[C:41]([OH:43])=[O:42]>C1COCC1.C(N(CC)CC)C>[C:1]([S:4][CH2:5][CH2:6][C:7]([N:9]1[C@H:13]([C:14]([N:39]2[CH2:46][CH2:45][CH2:44][C@H:40]2[C:41]([OH:43])=[O:42])=[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 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 145742L-ProlineHCID 13316857HCID 13316857, compound

Product 1

HCID 13316885HCID 13316885, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 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 solution of 1.0 g of L-proline and 1.0 g of triethylamine dissolved in aqueous THF is added, and treated in the same manner as Example 1 to give 1.5 g (68%) of the titled compound.

Workup

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

Sources & evidence

ORD record
ord-8f5123c3f0054d77a6642392c0d71a67
Source dataset
uspto-grants-1984_01
Patent number
US04425333

Reaction notes

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