Diisopropylethylamine → HCID 86639456, compound

HRID 451890Notes

Reaction equation

HRID 451890 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:38][CH2:39][CH2:40][OH:41])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([NH:17][C@@H:18]([CH2:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:19][N:20]([CH3:30])[C:21](=[O:29])[O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.Cl[C:52]([O:54][C:55]1[CH:60]=[CH:59][C:58]([N+:61]([O-:63])=[O:62])=[CH:57][CH:56]=1)=[O:53]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:38][CH2:39][CH2:40][O:41][C:52]([O:54][C:55]2[CH:56]=[CH:57][C:58]([N+:61]([O-:63])=[O:62])=[CH:59][CH:60]=2)=[O:53])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([NH:17][C@@H:18]([CH2:31][CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[CH2:19][N:20]([CH3:30])[C:21](=[O:29])[O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:28])[CH3:26])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 86639457HCID 86639457, compound

Product 1

HCID 86639456HCID 86639456, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(3-chlorophenyl)(2-hydroxyethoxy)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate (0.1880 g, 0.3 mmol, 1.0 equiv), DMAP (0.150 g, 1.2 mmol, 4 equiv), DIEA (1 mL, 6 mmol, 20 equiv), and 4-nitrophenyl chloroformate (0.1346 g, 0.67 mmol, 2.2 equiv) in CH2Cl2 (6 mL) was stirred at rt for 24 h. The reaction mixture was directly used in the next step without further purification. LC-MS (3 min) tR=2.68 min, m/z 777, 775 (MH+).

Workup

  1. customThe reaction mixture was directly used in the next step without further purification
  2. customLC-MS (3 min) tR=2.68 min, m/z 777, 775 (MH+)

Sources & evidence

ORD record
ord-43b04f6144374d5487e989968b5989e1
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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