4-Methylmorpholine → Azide

HRID 464901Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]([C:30]([NH:32][NH2:33])=[O:31])[CH2:24][C:25]1[N:29]=[CH:28][NH:27][CH:26]=1)=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:35][C@H](P(=O)(O)O)CC(C)C.[NH2:45][C@H:46]([P:51](=[O:54])([OH:53])[OH:52])[CH2:47][CH:48]([CH3:50])[CH3:49].CN1CCOCC1>CN(C)C=O>[N-:35]=[N+:32]=[N-:33].[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]([C:30]([NH:45][C@H:46]([P:51](=[O:53])([OH:52])[OH:54])[CH2:47][CH:48]([CH3:50])[CH3:49])=[O:31])[CH2:24][C:25]1[N:29]=[CH:28][NH:27][CH:26]=1)=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 4 °C

Procedure

An azide solution was prepared in the same way as in Example 8 using 0.45 g. (1 mmole) of N-benzyloxycarbonyl-L-phenylalanyl-L-histidine hydrazide. To the solution was added 0.20 g. (1 mmole) of 1(R)-amino-3-methylbutylphosphonic acid hemihydrochloride (melting at 267°-269.5°) prepared according to the method of J. R. Chambers and A. F. Isbell [J. Org. Chem., 29, 832 (1964)], followed by 0.11 g. of N-methylmorpholine. The mixture was stirred at 4° C. for 11 days. Insoluble matter was removed by filtration and the filtrate was treated in a conventional manner. There was obtained 0.47 g. of the desired compound as a white powdery solid, melting at 159°-167° C.; [α]22 -15.6° (C=0.5, dimethylformamide).

Workup

additionTo the solution was added 0.20 g
customInsoluble matter was removed by filtration
additionthe filtrate was treated in a conventional manner
customThere was obtained 0.47 g

Sources & evidence

ORD record: ord-c9365f4a9c9f4d9796e9af32e0883e40
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04548926

Reaction notes

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