(R)-3-((R)-2-amino-3-(6-(benzyloxy)-6-oxohexylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate → 6-((R)-2-amino-3-((R)-2,3-bis(dodecanoyloxy)propylthio)propanamido)hexanoic acid

HRID 2205005Notes

Reaction equation

HRID 2205005 reaction equation
[C:1]([O:14][CH2:15][C@@H:16]([O:40][C:41](=[O:53])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH2:17][S:18][CH2:19][C@H:20]([NH2:39])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31]CC1C=CC=CC=1)=[O:30])=[O:22])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>CCO.[Pd]>[NH2:39][C@@H:20]([CH2:19][S:18][CH2:17][C@H:16]([O:40][C:41](=[O:53])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH2:15][O:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:22]

Participants

4

Reactant 1

HCID 67416012(R)-3-((R)-2-amino-3-(6-(benzyloxy)-6-oxohexylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate

Product 1

HCID 534764336-((R)-2-amino-3-((R)-2,3-bis(dodecanoyloxy)propylthio)propanamido)hexanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-3-((R)-2-amino-3-(6-(benzyloxy)-6-oxohexylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate in EtOH (0.1 M) was added palladium black (2 eq). The reaction mixture was stirred under hydrogen (1 atm) overnight. The palladium was filtered off and the filtrate was concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM to give the product as an off-white solid. 1H NMR (CDCl3): δ 7.33 (t, 1H), 5.06-5.15 (m, 1H), 4.30 (dd, 1H), 4.08 (dd, 1H), 3.43 (dd, 1H), 3.20-3.31 (m, 1H), 3.09-3.19 (m, 1H), 3.04 (dd, 1H), 2.61-2.74 (m, 3H), 2.21-2.31 (m, 6H), 1.84-2.06 (m, 3H), 1.40-1.63 (m, 8H), 1.28-1.37 (m, 2H), 1.12-1.28 (m, 32H), 0.81 (t, 6H). LRMS [M+H]=673.5.

Workup

  1. filtrationThe palladium was filtered off
  2. concentrationthe filtrate was concentrated en vaccuo
  3. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-1ba2152bafc04873ad59e9aa63c5edb3
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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