4-Methylmorpholine → HCID 131718828, compound

HRID 1768875Notes

Reaction equation

HRID 1768875 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=[O:21])CC1C2C(=CC=CC=2)NC=1)=[O:7])([CH3:4])[CH3:3].[NH2:23][C@H:24]([C:29]([N:31]([CH3:43])[C@H:32]([C:40]([NH2:42])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27].ClC(OCC(C)C)=O.CN1CCOCC1>O1CCCC1>[CH3:4][C:2]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:40][C:32]1[NH:31][C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH:33]=1)=[O:7])([CH3:1])[CH3:3].[NH2:23][C@H:24]([C:29]([N:31]([CH3:43])[C@H:32]([C:40]([NH2:42])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30])[CH2:25][CH:26]([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 131718827HCID 131718827, compound

Product 1

HCID 131718828HCID 131718828, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Condensation of Boc-trp-OH (1.81 g.) and H-Leu-MePhe-NH2 and H-Leu-Mephe-NH2 (mixture of isomers) hydrochloride salt (1.95 g.) by the mixed anhydride method using isobutyl chloroformate (813 mg.) and N-methylmorpholine (two 685 mg. portions) in tetrahydrofuran (35 ml.) at -20° C. for 20 min. and then at room temperature briefly, isolation by ethyl acetate extraction, and purification by filtration through silica gel with ethyl acetate gave Boc-trp-Leu-MePhe-NH2 and Boc-trp-Leu-Mephe-NH2 (mixture of isomers) as white foam (2.70 g., 78% yield).

Workup

  1. customat -20° C.
  2. customfor 20 min.
  3. extractionat room temperature briefly, isolation by ethyl acetate extraction, and purification
  4. filtrationby filtration through silica gel with ethyl acetate

Sources & evidence

ORD record
ord-80caf7091f7a4ce58c113aecc0aeb5e3
Source dataset
uspto-grants-1995_01
Patent number
US05378803

Reaction notes

Loading…