Chlorosuccinimide → HCID 178453614, compound

HRID 1259441Notes

Reaction equation

HRID 1259441 reaction equation
[C:1]([O:5][C:6](=[O:40])[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](=[O:39])[NH:16][CH:17]([C:25]2[S:26][CH:27]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36](=[O:38])[NH2:37])=[CH:32][CH:31]=3)[CH:29]=2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Cl:48])C(=O)C1>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:40])[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](=[O:39])[NH:16][CH:17]([C:25]2[S:26][C:27]([Cl:48])=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36](=[O:38])[NH2:37])=[CH:32][CH:31]=3)[CH:29]=2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178453615HCID 178453615, compound

Product 1

HCID 178453614HCID 178453614, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1C (336 mg, 0.6 mmol) and NCS (104 mg, 0.78 mmol) in chloroform (20 mL) was stirred at 60° C. under N2. After 1.5 h, the mixture was cooled to rt and concentrated. Reverse-phase HPLC purification gave ID as a light yellow solid. LC/MS m/z 596.2 (M+H)+.

Workup

  1. temperaturethe mixture was cooled to rt
  2. concentrationconcentrated
  3. customReverse-phase HPLC purification
  4. customgave ID as a light yellow solid

Sources & evidence

ORD record
ord-d0647642d6b6477880eedc7142aad943
Source dataset
uspto-grants-2013_06
Patent number
US08466295B2

Reaction notes

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