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 1745013Notes

Reaction equation

HRID 1745013 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-98ba22d905ea443f9da6fb01008a29bd
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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