Hydrochloric Acid → 4-Methylmorpholine

HRID 464907Notes

Reaction equation

HRID 464907 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][NH2:37])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:38][N:39](C)C=O.Cl.N(OCCC(C)C)=O>O1CCOCC1>[CH3:38][N:26]1[CH2:24][CH2:12][O:35][CH2:34][CH2:27]1.[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([N:36]=[N+:37]=[N-:39])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8053Isoamyl NitriteHCID 178514450HCID 178514450, compound

Product 2

HCID 79724-MethylmorpholineHCID 178514641HCID 178514641, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 250 mg. (0.5 mmole) of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidine hydrazide in 8 ml. of dimethylformamide was added 0.42 ml. of a 4N solution of hydrochloric acid in dioxane, and the mixture was cooled to -60° C. 0.1 ml. of isopentyl nitrite was then added and the reaction temperature was raised to -20° C. After disappearance of the hydrazide had been confirmed, the temperature was lowered to -60° C. The mixture was neutralized with 0.17 g. of N-methylmorpholine to form a solution of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidine azide.

Workup

  1. customwas lowered to -60° C

Sources & evidence

ORD record
ord-b6f2d156a7084036a5bda51b6618a229
Source dataset
uspto-grants-1985_10
Patent number
US04548926

Reaction notes

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