Benzyl chloroformate → HCID 67870133, compound

HRID 486065Notes

Reaction equation

NC([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH2:15][C:16]1[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=1)=[CH:9][CH:8]=2)CC.[CH2:26]([O:33][C:34](Cl)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[CH2:26]([O:33][C:34]([NH:6][CH2:5][CH2:13][CH2:12][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[CH:11]=2)[NH:6][CH:5]=1)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-aminopropyl-5-(2-quinolylmethoxy)-indole (1.0 g) and benzyloxycarbonyl chloride (1.0 ml) in toluene was heated at 100° C. for 15 minutes. The cooled solution was concentrated in vacuo and the resultant product purified by chromatographed on silica gel using 30%-ethyl acetate in n-hexanes as eluent to yield 1-(3-(benzyloxycarbonylamino-n-propyl)-5-(2-quinolylmethoxy)-indole (0.27 g), m.p. 109°-111° C.

Workup

concentrationThe cooled solution was concentrated in vacuo
customthe resultant product purified
customby chromatographed on silica gel using 30%-ethyl acetate in n-hexanes as eluent

Sources & evidence

ORD record: ord-e7827bc7e0694b2ebc79530e70c80afa
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05290788

Reaction notes

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