Dichloromethane → HCID 18653506, compound

HRID 1728392Notes

Reaction equation

[CH3:1][C:2]([O:5][C:6](=[O:38])[CH:7]([NH:22][CH:23]([C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH2:20])[CH:16]=2)[C:11]1=[O:21])([CH3:4])[CH3:3].ClCCl.[C:42]1([S:48](Cl)(=[O:50])=[O:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>N1C=CC=CC=1>[CH3:1][C:2]([O:5][C:6](=[O:38])[C@H:7]([NH:22][C@H:23]([C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:20][S:48]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)(=[O:50])=[O:49])[CH:16]=2)[C:11]1=[O:21])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

58 mg of 2-[1-(benzylamino)carbonyl-3-methyl-butylamino]-4-(5-amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butanoic acid-1,1-dimethylethyl ester, prepared as in Example 73 where the protecting group Rp, 1,1-dimethylethyl, was not removed following the condensation reaction seen in Scheme 2, was added to 4 mL dichloromethane under nitrogen. The mixture was cooled to 0° C. and 0.015 mL benzenesulfonyl chloride was added immediately followed by 0.1 mL pyridine. The mixture was allowed to warm to room temperature and was stirred for 18 h. The solvent was removed by evaporation and the residue was purified by reverse phase H.P.L.C. The solvent was removed by evaporation to afford the title compound; 31.8 mg

Workup

customwas not removed
customthe condensation reaction
temperatureto warm to room temperature
customThe solvent was removed by evaporation
customthe residue was purified by reverse phase H.P.L.C
customThe solvent was removed by evaporation

Sources & evidence

ORD record: ord-0bb8482208234051a74b9f17400456d6
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326760

Reaction notes

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