tert-butyl (2S,4EZ)-2-({[(2S)-2-hydroxy-2-phenylethyl]amino}carbonyl)-4-(methoxyimino)-1-pyrrolidine-carboxylate → (2S,4EZ)-N-[(2S)-2-hydroxy-2-phenylethyl]-4(methoxyimino)-2-pyrrolidinecarboxamide

HRID 1349013Notes

Reaction equation

HRID 1349013 reaction equation
[OH:1][C@@H:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][NH:4][C:5]([C@@H:7]1[CH2:11][C:10](=[N:12][O:13][CH3:14])[CH2:9][N:8]1C(OC(C)(C)C)=O)=[O:6]>C(Cl)Cl>[OH:1][C@@H:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][NH:4][C:5]([C@@H:7]1[CH2:11][C:10](=[N:12][O:13][CH3:14])[CH2:9][NH:8]1)=[O:6]

Participants

3

Reactant 1

HCID 131725396tert-butyl (2S,4EZ)-2-({[(2S)-2-hydroxy-2-phenylethyl]amino}carbonyl)-4-(methoxyimino)-1-pyrrolidine-carboxylate

Product 1

HCID 131725397(2S,4EZ)-N-[(2S)-2-hydroxy-2-phenylethyl]-4(methoxyimino)-2-pyrrolidinecarboxamideYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution was made containing the amide compounds from the previous step, e.g. tert-butyl (2S,4EZ)-2-({[(2S)-2-hydroxy-2-phenylethyl]amino}carbonyl)-4-(methoxyimino)-1-pyrrolidinecarboxylate (2.64 g, 7 mmol), in anhydrous DCM (35 ml). At 0° C., HCl gas was bubbled slowly through the reaction and the deprotection was followed by TLC. After approximately 20 minutes, the DCM was evaporated. The product was concentrated in vacuo from DCM (2–3 times) to remove the HCl. The desired product, e.g. (2S,4EZ)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide (1.94 g, quant.) was isolated as a yellow solid and used without further purification.

Workup

  1. customAt 0° C., HCl gas was bubbled slowly through the reaction
  2. customthe DCM was evaporated
  3. concentrationThe product was concentrated in vacuo from DCM (2–3 times)
  4. customto remove the HCl

Sources & evidence

ORD record
ord-71f567fd2a0c49ee86dff75f483503b2
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

Loading…