Ethanolamine → HCID 86758009, compound

HRID 844340Notes

Reaction equation

HRID 844340 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=1)[CH2:5][NH:6][C:7]([O:9][CH2:10][C@@H:11]1[C@@H:15]([O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[CH2:14][C@@H:13]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[C@H:12]1[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][C:36](O)=[O:37])=[S:8].C(N(CC)CC)C.C(OC(Cl)=O)C.[CH2:55]([CH2:57][NH2:58])[OH:56]>C(Cl)Cl.CCOC(C)=O>[OH:56][CH2:55][CH2:57][NH:58][C:36]([CH2:35][CH2:34][CH2:33]/[CH:32]=[CH:31]\[CH2:30][C@H:12]1[C@@H:13]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:14][C@@H:15]([O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C@@H:11]1[CH2:10][O:9][C:7](=[S:8])[NH:6][CH2:5][C:4]1[CH:39]=[CH:40][CH:41]=[C:2]([Cl:1])[CH:3]=1)=[O:37]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 86585191HCID 86585191, compound

Product 1

HCID 86758009HCID 86758009, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of acid 7 (60 mg, 0.10 mmol) and triethylamine (30 mg, 0.30 mmol) in CH2Cl2 (2 mL) was cooled to 0° C. and ethylchloroformate (11 μL, 0.12 mmol) was added. After 0.5 h ethanolamine (7.2 μL, 0.12 mmol) was added and the reaction was allowed to warm to room temperature for 12 h. The reaction was diluted with EtOAc and washed with 1N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 100% EtOAc followed by 19:1 EtOAc/MeOH) provided 40 mg of the above titled compound.

Workup

  1. washwashed with 1N HCl, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic portion was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash column chromatography (silica gel, 100% EtOAc followed by 19:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-cd81672681e54521a1a67c413546d60d
Source dataset
uspto-grants-2002_04
Patent number
US06380250B1

Reaction notes

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