Benzyl bromoacetate → N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester

HRID 1757819Notes

Reaction equation

HRID 1757819 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[C:6]([NH2:29])[CH:5]=1.Br[CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].CN(C)[C:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][C:53]=2N(C)C)C=CC=1.[Na]>CN(C=O)C.C(#N)C>[C:37]1([CH2:36][O:35][C:33](=[O:34])[CH2:32][N:29]([C:6]2[CH:7]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:30])[CH:5]=2)[CH2:4][C:3](=[O:2])[O:30][CH2:45][C:54]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 5360545SodiumHCID 193890883-Amino-5-(octadecyloxy)benzoic acid methyl ester

Product 1

HCID 19388997N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl esterYield 93.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3.25 g (7.74 mmol) of 3-amino-5-(octadecyloxy)benzoic acid methyl ester, 3.7 ml (23 mmol) of benzyl bromoacetate, 4.2 g (19.4 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.3 g (2.2 mmol) of sodium iodidein 65 ml of acetonitrile and 20 ml of DMF was stirred and heated at reflux under argon for 48 hours. The reaction mixture was concentrated at reducedpressure and ethyl acetate was added to the residue. The extract was washedwith 0.05N HCl, with saturated NaHCO3 solution, dried and concentratedat reduced pressure to a solid which was purified by HPLC using 15% ethyl acetate-hexane to give 2.6 g (48% yield, mp 62°-63°) of N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy) ethyl]glycine phenylmethyl ester.

Workup

  1. temperatureheated
  2. temperatureat reflux under argon for 48 hours
  3. concentrationThe reaction mixture was concentrated at reducedpressure and ethyl acetate
  4. additionwas added to the residue
  5. customdried
  6. customconcentratedat reduced pressure to a solid which was purified by HPLC

Sources & evidence

ORD record
ord-1801597085ba4c198290f1eed2b67f05
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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