Diazomethane → HCID 53955469, compound

HRID 2226597Notes

Reaction equation

[CH2:1]([N:6]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:29])[CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:11]([C:30]([OH:32])=[O:31])[CH2:10]1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].[N+](=[CH2:40])=[N-]>CO.C(OCC)C>[CH2:33]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:29])[CH:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:11]([C:30]([O:32][CH3:40])=[O:31])[CH2:10]1)=[O:8])[CH2:34][CH2:35][CH2:36][CH3:37]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 368 mg (0.725 mmole) of (S)-4-(dipentylcarbamoyl)-1-(diphenylacetyl)piperazine-2carboxylic acid (from Example 9) in 5 ml of methanol was treated at 0° C. with 20 ml of diazomethane solution in diethyl ether (prepared by the procedure above). The solution was stirred at 0° C. for 30 minutes and at 25° C. for 30 minutes. The excess diazomethane was destroyed by the dropwise addition of acetic acid until the solution became colorless. The resulting solution was concentrated in vacuo and the residue was chromatographed over an 85×2.5 cm LH-20 column and concentrated in vacuo to 225 mg (59%) of pale colored oil which was homogeneous by TLC (1:1 hexane-ethyl acetate, Rf =0.7).

Workup

customprepared by the procedure above)
customThe excess diazomethane was destroyed by the dropwise addition of acetic acid until the solution
concentrationThe resulting solution was concentrated in vacuo
customthe residue was chromatographed over an 85×2.5 cm LH-20 column
concentrationconcentrated in vacuo to 225 mg (59%) of pale colored oil which

Sources & evidence

ORD record: ord-54b74f756feb4e8faecfdc31c0b8fa72
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05348955

Reaction notes

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