Palmitoyl chloride → (R)-tert-butyl 3-((R)-2,3-bis(decylcarbamoyloxy)propylthio)-2-palmitamidopropanoate

HRID 2407961Notes

Reaction equation

HRID 2407961 reaction equation
[NH2:1][C@@H:2]([CH2:10][S:11][CH2:12][C@H:13]([O:29][C:30](=[O:42])[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:14][O:15][C:16](=[O:28])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].CCN(C(C)C)C(C)C.[C:52](Cl)(=[O:68])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67]>C(Cl)Cl>[CH2:32]([NH:31][C:30]([O:29][C@H:13]([CH2:14][O:15][C:16](=[O:28])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:12][S:11][CH2:10][C@H:2]([NH:1][C:52](=[O:68])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])=[O:42])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 81531DiisopropylethylamineHCID 86678326(R)-tert-butyl 2-amino-3-((R)-2,3-bis(decylcarbamoyloxy)propylthio)propanoate

Product 1

HCID 86678327(R)-tert-butyl 3-((R)-2,3-bis(decylcarbamoyloxy)propylthio)-2-palmitamidopropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 2-amino-3-((R)-2,3-bis(decylcarbamoyloxy)propylthio)propanoate in dry DCM (0.1 M) at 0° C. was added DIEA (1.2 eq) and palmitoyl chloride (1.1 eq). The reaction was allowed to warm to room temperature then stirred for 16 hours. The crude reaction was then concentrated and purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient 0-60% EtOAc/Hex to afford the title compound as a white solid.

Workup

  1. customThe crude reaction
  2. concentrationwas then concentrated
  3. custompurified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-f6f380395b524211b232e2acded7f81c
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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