Dichloromethane → Ammonia

HRID 412641Notes

Reaction equation

HRID 412641 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][C@H:19]1[CH2:23][CH2:22][NH:21][CH2:20]1)=[O:17].Br[CH2:25][C:26]([NH2:28])=[O:27].ClCCl>CO>[NH3:3].[NH2:28][C:26]([CH2:25][N:21]1[CH2:22][CH2:23][C@H:19]([NH:18][C:16]([C@@H:11]2[CH2:12][CH2:13][CH2:14][CH2:15][N:10]2[C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[O:17])[CH2:20]1)=[O:27]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 696322-BromoacetamideHCID 57068119(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-pyrrolidin-3-yl]-2-piperidinecarboxamide

Product 2

HCID 222AmmoniaHCID 57103398(2S)-N2-[(3S)-1-((aminocarbonyl)methyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by a similar method to Example 5 from (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-pyrrolidin-3-yl]-2-piperidinecarboxamide [see Example 4] and 2-bromoacetamide. The crude product was purifies by column chromotography on silica gel eluting with a solvent gradient of 93:7:1, changing to 90:10:1, by volume, dichloromethane:methanol:0.88 aqueous ammonia solution to afford (2S)-N2-[(3S)-1-((aminocarbonyl)methyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide as an oil.

Sources & evidence

ORD record
ord-f79c04ce761b470d93e47927453ad33b
Source dataset
uspto-grants-2003_05
Patent number
US06562964B1

Reaction notes

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