Pyrrolidine, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3S)- → HCID 71093530, compound

HRID 632405Notes

Reaction equation

HRID 632405 reaction equation
[CH3:1][C:2]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)[N:14]=1)=[O:12])([C:4]1[N:8]=[C:7]([CH3:9])[O:6][N:5]=1)[CH3:3].CC([Si](C)(C)[O:30][C@H:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)(C)C>>[CH3:1][C:2]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([N:33]2[CH2:34][CH2:35][C@H:31]([OH:30])[CH2:32]2)=[C:15]([O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)[N:14]=1)=[O:12])([C:4]1[N:8]=[C:7]([CH3:9])[O:6][N:5]=1)[CH3:3]

Participants

3

Reactant 2

HCID 15385422Pyrrolidine, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3S)-HCID 710935455-Bromo-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

Product 1

HCID 71093530HCID 71093530, compound

Procedure

The title compound was synthesized in analogy to Example 322b, using 5-bromo-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide (Example 322a) and (35)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-pyrrolidine (CAN 207113-36-8) as starting materials. The protecting group was removed with tetrabutylammonium fluoride in THF; LC-MS (UV peak area/ESI) 100%, 402.2134 (M+H)+.

Workup

  1. customThe protecting group was removed with tetrabutylammonium fluoride in THF

Sources & evidence

ORD record
ord-e22ee84b17224ed8ac13ecca103911e2
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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