(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid → HCID 68811255, compound

HRID 2375265Notes

Reaction equation

HRID 2375265 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[F:18][C@H:19]1[C@@H:23]([F:24])[CH2:22][NH:21][CH2:20]1>>[F:18][C@H:19]1[C@@H:23]([F:24])[CH2:22][N:21]([C:10]([C@@H:9]2[CH2:13][C@@H:14]([OH:16])[CH2:15][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:12])[CH2:20]1

Participants

3

Reactant 2

HCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 66880882(3R,4S)-3,4-Difluoropyrrolidine--hydrogen chloride (1/1)

Product 1

HCID 68811255HCID 68811255, compoundYield 67.1%

Procedure

(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline (2.31 g, 10 mmol), was coupled with (3R,4S) -rel-3,4-difluoropyrrolidine hydrochloride (1.44 g, 10 mmol, Preparation 4), in a manner analogous to that described in Preparation 1, Step 1, to afford 2.15 g (67%) of the title product as an off-white foam. MS m/z 321 (MH+).

Workup

  1. customthat described in Preparation 1, Step 1

Sources & evidence

ORD record
ord-17f5f9255b5a47158de7d2f586ed24f6
Source dataset
uspto-grants-2008_12
Patent number
US07465732B2

Reaction notes

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