Diisopropylethylamine → Benzyl (R)-3-((R)-2,3-didodecanamidopropylthio)-1-(1-(hydroxymethyl)cyclopropylamino)-1-oxopropan-2-ylcarbamate

HRID 2204983Notes

Reaction equation

HRID 2204983 reaction equation
[C:1]([NH:14][C@H:15]([CH2:34][NH:35][C:36](=[O:48])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:16][S:17][CH2:18][C@@H:19]([C:31]([OH:33])=O)[NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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].Cl.[NH2:50][C:51]1([CH2:54][OH:55])[CH2:53][CH2:52]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:1]([NH:14][C@H:15]([CH2:34][NH:35][C:36](=[O:48])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:16][S:17][CH2:18][C@H:19]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:31]([NH:50][C:51]1([CH2:54][OH:55])[CH2:53][CH2:52]1)=[O:33])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14146222(1-Aminocyclopropyl)methanol hydrochlorideHCID 71294513(5R,9R)-9-dodecanamido-3,12-dioxo-1-phenyl-2-oxa-7-thia-4,11-diazatricosane-5-carboxylic acid

Product 1

HCID 86678280Benzyl (R)-3-((R)-2,3-didodecanamidopropylthio)-1-(1-(hydroxymethyl)cyclopropylamino)-1-oxopropan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5R,9R)-9-dodecanamido-3,12-dioxo-1-phenyl-2-oxa-7-thia-4,11-diazatricosane-5-carboxylic acid (1 eq) in DCM (0.1 M) was added (1-aminocyclopropyl)methanol hydrochloride (1.3 eq), DIEA (2.5 eq) and HBTU (1.2 eq). The reaction was stirred at room temperature for 2 hours then concentrated and purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-100% EtOAc/Hex, then 0-10% MeOH/DCM to afford the title compound as an off-white solid.

Workup

  1. concentrationthen concentrated
  2. custompurified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-2908e8020b754364b928af7c424545ae
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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