4-Methylmorpholine → Boc-(D)-Ala-Gly-MePhe-Leu-OMe

HRID 1390157Notes

Reaction equation

HRID 1390157 reaction equation
[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:2]([C:4]([NH:6][CH2:7][C:8]([OH:10])=O)=[O:5])[CH3:3].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[NH:33]([CH3:54])[C@H:34]([C:42]([NH:44][C@H:45]([C:50]([O:52][CH3:53])=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(C)[C@H](C(N[C@H](C(OC)=O)CC(C)C)=O)CC1C=CC=CC=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C(Cl)Cl>C1COCC1.CN(C=O)C>[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:2]([C:4]([NH:6][CH2:7][C:8]([N:33]([CH3:54])[C@H:34]([C:42]([NH:44][C@H:45]([C:50]([O:52][CH3:53])=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:10])=[O:5])[CH3:3]

Participants

9

Reactant 6

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 12944592(N-Boc-D-alanyl)-glycineHCID 13918317Boc-MePhe-Leu-OMeHCID 13945171H-MePhe-Leu-OMeHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 131712075Boc-(D)-Ala-Gly-MePhe-Leu-OMe

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 24.6 g of Boc-(D)-Ala-Gly-OH and 11.2 ml of N-methylmorpholine in 400 ml of THF are added 13.2 ml of chloroformic acid isobutyl ester at -25°. After 5 minutes, at 25°, 11.2 ml of N-methyl-morpholine and 42.1 g of H-MePhe-Leu-OMe (trifluoroacetate) in DMF [which has previously been prepared by the treatment of Boc-MePhe-Leu-OMe with TFA-methylene chloride (1:1)] are added. After 2 hours, at -15°, the title compound is isolated as described under (a) above, as a solid foam.

Workup

  1. additionare added
  2. waitAfter 2 hours

Sources & evidence

ORD record
ord-5407d542daed4a63b994859e86ba853c
Source dataset
uspto-grants-1981_01
Patent number
US04247543

Reaction notes

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