Hydrochloric Acid → HCID 131723106, compound

HRID 480546Notes

Reaction equation

HRID 480546 reaction equation
[CH2:1]([N:19]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:20](=[O:37])[CH2:21][O:22][C:23](=[O:36])[CH2:24][NH:25]C(OCC1C=CC=CC=1)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[ClH:56].CO>CCOC(C)=O.[Pd]>[ClH:56].[CH2:38]([N:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:20](=[O:37])[CH2:21][O:22][C:23](=[O:36])[CH2:24][NH2:25])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 54147379HCID 54147379, compound

Product 1

HCID 131723106HCID 131723106, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd/C (150 mg) was added to a solution of N-[(phenylmethoxy)-carbonyl]glycine [2-(dioctadecylamino)-2-oxoethyl]ester (1.2 g; 1.4 mmol) in EtOAc (100 mL) and the suspension was stirred for 3 h under hydrogen atmosphere at room temperature. After filtration (through a Millipore® filter FT 0.45 μm) 1.2 M HCl in MeOH (1.3 mL; 1.6 mmol) was added dropwise to the resulting solution obtaining the precipitation of a white solid that was filtered to give the desired compound (830 mg; 1.2 mmol).Yield 86%. HPLC: 100% (area %). K.F.: 0.22%. The MS and IR spectra were consistent with the structure.

Workup

  1. filtrationAfter filtration (through a Millipore®
  2. additionwas added dropwise to the resulting solution
  3. customobtaining
  4. customthe precipitation of a white solid
  5. filtrationthat was filtered

Sources & evidence

ORD record
ord-98d91728f7944b1094f74eb3bf040c0f
Source dataset
uspto-grants-2003_11
Patent number
US06652834B2

Reaction notes

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