Dimethylformamide → HCID 20792949, compound

HRID 2184377Notes

Reaction equation

C([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[C@H:9]1[C:14](O)=[O:15])(OC(C)(C)C)=O.[C:17](=[O:20])(O)[O-:18].[NH4+:21].C1(N=C=N[CH:31]2[CH2:36][CH2:35]CCC2)CCCCC1.[CH3:37]N(C=O)C>>[C:17]([NH:21][C:14]([C@@H:9]1[C@@H:10]([OH:13])[CH2:11][CH2:12][NH:8]1)=[O:15])([O:18][C:36]([CH3:35])([CH3:31])[CH3:37])=[O:20]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 10868Dicyclohexylcarbodiimide

HCID 14013Ammonium Bicarbonate

HCID 14037017(2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 20792949HCID 20792949, compound

Conditions

Temperature: 20 °C

Procedure

To N-Boc-(2S,3S)-3-hydroxypyrrolidine-2-carboxylic acid (1.36 g) in DMF (6 ml) added ammonium bicarbonate (0.5 g) and dicyclohexylcarbodiimide (1.3 g). After stirring at 20° C. for 20 h the reaction was concentrated by evaporation under reduced pressure, and the residue triturated with ethyl acetate. The soluble material was purified by chromatography on silica eluting with 50-100% (5% acetic acid in diethyl ether) in hexane to give the title material as a colourless gum, (0.5 g). NMR (CD3OD) major rotamer: 1.43, (s, 9H), 1.88 (m, 1H), 2.0 (m, 1H), 3.55 (m, 2H), 4.03(s, 1H), 4.31 (bs, 1H); minor rotamer: 1.47, (s, 9H), 1.7 (m, 1H), 2.0 (m, 1H), 3.55 (m, 2H), 4.09(s, 1H), 4.34 (d, J=4 Hz, 1H).

Workup

concentrationwas concentrated by evaporation under reduced pressure
customthe residue triturated with ethyl acetate
customThe soluble material was purified by chromatography on silica eluting with 50-100% (5% acetic acid in diethyl ether) in hexane

Sources & evidence

ORD record: ord-4351c80eb2c343eaa6f4b2587640e825
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900345B2

Reaction notes

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