Hydrazine hydrate (1:1) → HCID 13728032, compound

HRID 1906195Notes

Reaction equation

[CH2:1]([O:19][CH2:20][CH:21]([N:43]1C(=O)C2=CC=CC=C2C1=O)[CH2:22][O:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O.NN>C(O)(C)C>[CH2:1]([O:19][CH2:20][CH:21]([NH2:43])[CH2:22][O:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 70 °C

Procedure

In 50 ml of isopropylalcohol was dissolved 6.4 g of 3-octadecyloxy-2-phthalimido-1-trityloxypropane, and 4 ml of hydrazine hydrate was added to the solution. The mixture was heated at 70° C. for 1 hour, and concentrated under reduced pressure. Ethyl acetate was added to the residue and the insoluble matter was filtered off. The filtrate was concentrated to dryness and purified by silica gel chromatography (eluent: n-hexane-ethyl acetate=3:1) to give 4.41 g (84%) of the desired compound as a pale brown solid.

Workup

additionwas added to the solution
concentrationconcentrated under reduced pressure
additionEthyl acetate was added to the residue
filtrationthe insoluble matter was filtered off
concentrationThe filtrate was concentrated to dryness
custompurified by silica gel chromatography (eluent: n-hexane-ethyl acetate=3:1)

Sources & evidence

ORD record: ord-c5f50be578404c26a53f7f550bea3989
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04650791

Reaction notes

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