Hydrochloric Acid → HCID 67148598, compound

HRID 2428129Notes

Reaction equation

HRID 2428129 reaction equation
Cl.C(OC(=O)[N:8]([CH2:12][C:13]1[CH:18]=[C:17]([CH2:19][C:20](=[O:24])[NH:21][CH2:22][CH3:23])[CH:16]=[CH:15][C:14]=1[Cl:25])[CH:9]1[CH2:11][CH2:10]1)(C)(C)C.[OH-].[Na+]>C(Cl)Cl>[Cl:25][C:14]1[CH:15]=[CH:16][C:17]([CH2:19][C:20]([NH:21][CH2:22][CH3:23])=[O:24])=[CH:18][C:13]=1[CH2:12][NH:8][CH:9]1[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67148690HCID 67148690, compound

Product 1

HCID 67148598HCID 67148598, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

HCl (4M in dioxane, 29 m-L) was added to a sol. of (2-chloro-5-ethylcarbamoylmethyl-benzyl)-cyclopropyl-carbamic acid tert-butyl ester (2.94 g, 8.01 mmol) in CH2Cl2 (29 mL) at 0° C. The mixture was stirred for 2 h at 0° C., and was carefully neutralized with aq. 1M NaOH. The layers were separated, and the aq. layer was extracted with CH2Cl2. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to yield the crude title compound (1.90 g, 89%) that was used further without purification. LC-MS: tR=0.58 min; ES+: 308.03.

Workup

  1. customThe layers were separated
  2. extractionthe aq. layer was extracted with CH2Cl2
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-057e647cb70b48dc9a802cd064baf7ac
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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