Ammonium Chloride → (S)-[(N-Methoxy-N-methylcarbamoyl)phenylmethyl]carbamic Acid Benzyl Ester

HRID 18834Notes

Reaction equation

HRID 18834 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:19]([OH:21])=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:35][NH:36][O:37][CH3:38].[Cl-].[NH4+]>ClCCl.CCOC(C)=O>[CH2:7]([O:8][C:9](=[O:10])[NH:11][C@H:12]([C:19](=[O:21])[N:36]([O:37][CH3:38])[CH3:35])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 819214Z-Phg-OH

Product 1

HCID 59655336(S)-[(N-Methoxy-N-methylcarbamoyl)phenylmethyl]carbamic Acid Benzyl EsterYield 98.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Z-L-phenylglycine (5.0 g, 17.5 mmol) in dichloromethane (35 mL) is added 1,1′-carbonyldimidazole (3.13 g, 19.3 mmol), and the solution is stirred at rt for 0.5 h. To the solution is added N,O-dimethylhydroxylamine hydrochloride (1.88 g, 19.3 mmol), and the mixture is stirred at rt overnight. To the reaction mixture is added ammonium chloride solution and EtOAc, and the organic layer is separated, washed with brine, dried (MgSO4), and filtered. The filtrate is evaporated to give 5.65 g of the product 482. 1H NMR (CDCl3) δ 7.50-7.20 (m, 10 H), 6.10 (d, 1 H), 5.78 (d, 1 H), 5.20-5.00 (m, 2 H), 3.43 (s, 3 H), 3.18 (s, 3 H); MS: m/z 329 (M++1).

Workup

  1. stirringthe mixture is stirred at rt overnight
  2. customthe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-323f5212d2af40ef941edd2329943efd
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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