Dichloromethane → HCID 18653510, compound

HRID 1728391Notes

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.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>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:43]([CH3:42])(=[O:45])=[O:44])[CH:16]=2)[C:11]1=[O:21])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

100 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 5 mL dichloromethane under nitrogen. The mixture was cooled to 0° C. and 0.1 mL of pyridine was added, followed by 0.014 mL methanesulfonyl chloride. The mixture was allowed to warm to room temperature and was stirred overnight. 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 give the title compound; 45 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-d780c4d5773841eb870410d8cf25ea9e
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326760

Reaction notes

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