Ethyl Acetate → HCID 70293374, compound

HRID 1872814Notes

Reaction equation

HRID 1872814 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([N:41]=[C:42]=[O:43])[C:15]([O:17][C@@H:18]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:19][C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:44][NH:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1.C(OCC)(=O)C>ClCCl>[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([NH:41][C:42]([N:45]([CH3:44])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1)=[O:43])[C:15]([O:17][C@@H:18]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:19][C:20]([O:22][CH2:23][C:24]([Cl:26])([Cl:25])[Cl:27])=[O:21])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 207272-Pyridinamine, N-methyl-HCID 57065864HCID 57065864, compound

Product 1

HCID 70293374HCID 70293374, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3S)-(2,2,2-trichloroethyl) 3-[(2S)-5-benzyloxycarbonyl-2-isocyanatopentanoyl]oxyhexadecanoate (0.33 g) and 2-(methylamino)pyridine (113 mg) in dichloromethane (5 ml) was stirred at room temperature overnight. The mixture was poured into ethyl acetate (20 ml), and washed with aqueous 1 N-hydrochloric acid (20 ml×2), saturated sodium bicarbonate (20 ml), and brine (20 ml). Then, the solution was dried over magnesium sulfate, and evaporated to dryness. The residue was chromatographed on a silica gel to give (3S)-(2,2,2-trichloroethyl) 3-[(2S)-5-benzyloxycarbonyl-2-{3-methyl-3-(2-pyridyl)ureido}pentanoyl]oxyhexadecanoate (0.25 g).

Workup

  1. washwashed with aqueous 1 N-hydrochloric acid (20 ml×2), saturated sodium bicarbonate (20 ml), and brine (20 ml)
  2. dry with materialThen, the solution was dried over magnesium sulfate
  3. customevaporated to dryness
  4. customThe residue was chromatographed on a silica gel

Sources & evidence

ORD record
ord-a5537c484dd34edbb8a746823a962d0e
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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