Triethylamine → HCID 53862937, compound

HRID 2165298Notes

Reaction equation

HRID 2165298 reaction equation
[C:1]([O:7][CH2:8][O:9][C:10]([C@@H:12]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:13][C@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15](Cl)=[O:16])=[O:11])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47].C(N(CC)CC)C>C(Cl)Cl>[CH2:49]([O:48][C:46](=[O:47])[CH2:45][CH2:44][NH:43][C:15](=[O:16])[C@@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13][C@@H:12]([C:10]([O:9][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 135021004-Methylbenzene-1-sulfonic acid--benzyl beta-alaninate (1/1)HCID 149971364-(Pivaloyloxymethoxycarbonyl)-2,4-(R*,R*)-dibenzylbutyryl chloride

Product 1

HCID 53862937HCID 53862937, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(Pivaloyloxymethoxycarbonyl)-2,4-(R*,R*) -dibenzylbutyryl chloride (1.2 g) in 10 ml of methylene chloride is added slowly to a solution of 1.15 g of benzyl 3-aminopropionate p-toluenesulfonic acid salt and 0.46 ml of triethylamine in 20 ml of methylene chloride. The reaction is stirred overnight at room temperature. The solution is washed with 2N hydrochloric acid, then with saturated sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated to give N-[4-pivaloyloxymethoxycarbonyl-(R*,R*)-2,4-dibenzylbutyryl]-3-aminopropionic acid benzyl ester.

Workup

  1. washThe solution is washed with 2N hydrochloric acid
  2. dry with materialwith saturated sodium bicarbonate, dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a75e882c7df4f23bf75803d70240361
Source dataset
uspto-grants-1990_07
Patent number
US04939261

Reaction notes

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