Triethylamine → HCID 86663951, compound

HRID 576884Notes

Reaction equation

HRID 576884 reaction equation
[NH2:1][CH2:2][C:3]1([C:9]([NH:11][O:12][C@@H:13]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:27][CH:26]=2)[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:39]([N:46]=[C:47]=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(N(CC)CC)C>ClCCl>[CH2:32]([O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][C@H:13]([O:12][NH:11][C:9]([C:3]2([CH2:2][NH:1][C:47]([NH:46][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:48])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)=[O:10])[C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])=[CH:26][CH:27]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76639Benzyl isocyanateHCID 86663952HCID 86663952, compound

Product 1

HCID 86663951HCID 86663951, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-benzyl 2-(1-(aminomethyl)cyclohexanecarboxamidooxy)-3-(4-(benzyloxy)phenyl)propanoate in dichloromethane 9 ml, benzyl isocyanate 143 μl (1.16 mmol) and triethylamine 271 μl (1.94 mmol) were added and the mixture was stirred at room temperature overnight. The reaction mixture was washed with water 10 ml and brine 10 ml. Then the organic phase was dried over magnesium sulfate, filtered and concentrated. The crude residue was purified on silica gel column chromatography (Merck 60N spherical, neutral elution by n-hexane:ethylacetate=100:0 to 70:30) to obtain the title compound 257 mg (41%).

Workup

  1. washThe reaction mixture was washed with water 10 ml and brine 10 ml
  2. dry with materialThen the organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified on silica gel column chromatography (Merck 60N spherical, neutral elution by n-hexane:ethylacetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-e5740a036719427db18a9ac1289e17eb
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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