Hydrochloric Acid → Sarcosine p-nitrobenzyl ester hydrochloride

HRID 891693Notes

Reaction equation

HRID 891693 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][O:9][C:10](=[O:21])[CH2:11][N:12](C(OC(C)(C)C)=O)[CH3:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[ClH:24].C(OCC)C>O1CCOCC1>[ClH:24].[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10](=[O:21])[CH2:11][NH:12][CH3:13])=[CH:22][CH:23]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69544076(N-t-butoxycarbonyl-N-methyl-amino)acetic acid p-nitrobenzyl ester

Product 1

HCID 69544074Sarcosine p-nitrobenzyl ester hydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (N-t-butoxycarbonyl-N-methyl-amino)acetic acid p-nitrobenzyl ester (4.30 g, 133 mmol) (obtained as described in Reference Example 43(1)) was added a solution of 4N hydrogen chloride in 1,4-dioxane (4.3 ml) in an ice bath, and the mixture was stirred at room temperature for 2.5 hours. After checking the completion of the reaction, diethyl ether was added thereto and the reaction mixture was stirred for 30 minutes. The resulting reaction mixture was filtered and the obtained residue was washed with diethyl ether and dried to give sarcosine p-nitrobenzyl ester hydrochloride (3.04 g, yield 88%).

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred for 30 minutes
  3. customThe resulting reaction mixture
  4. filtrationwas filtered
  5. washthe obtained residue was washed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-e27e02e2e6ed459a9aa1d3e6ac0636d7
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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