4-Methylmorpholine → HCID 15024522, compound

HRID 617708Notes

Reaction equation

HRID 617708 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18](O)=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:43][C:44]([C:47]([O:49][CH3:50])=[O:48])([CH3:46])[CH3:45].Cl.CN1CCOCC1>C(Cl)Cl.CN(C=O)C>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([NH:43][C:44]([C:47]([O:49][CH3:50])=[O:48])([CH3:46])[CH3:45])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 15024522HCID 15024522, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing about 1.5 g of Boc-Tyr(OBn)-OH (5) in 10 ml of dry CH2Cl2 was treated at 0° C. with about 417 mg of DCC. The mixture was stirred at 0° C. for about 5 minutes and treated with a solution containing about 620 mg of Aib-OMe hydrochloride (6) and about 490 mg of NMM in 2 ml of dry DMF. After stirring at 22° C. for about 12 hours, the reaction mixture was extracted with a saturated aqueous solution of NH4Cl. The organic layer was dried over Na2SO4, evaporated to dryness, and the residue chromatographed on SiO2 (EtOAc/hexanes 3:7) to yield about 900 mg of compound 7.

Workup

  1. additiontreated with a solution
  2. stirringAfter stirring at 22° C. for about 12 hours
  3. extractionthe reaction mixture was extracted with a saturated aqueous solution of NH4Cl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customthe residue chromatographed on SiO2 (EtOAc/hexanes 3:7)

Sources & evidence

ORD record
ord-49903caab619444aa81fd99d430a596a
Source dataset
uspto-grants-1999_09
Patent number
US05952294

Reaction notes

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