Triethylamine → HCID 57285391, compound

HRID 1395051Notes

Reaction equation

HRID 1395051 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)[CH2:10]1.C(N(CC)CC)C.ClC(OCC)=O.Cl.[CH3:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH:43][NH2:44]>C(Cl)Cl>[CH3:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH:43][NH:44][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[CH2:10][C@@H:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 1607888-(2-Octylcyclopropyl)octanoic acid

Product 1

HCID 57285391HCID 57285391, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.0 g of dihydrosterculic acid* in 75 ml methylene chloride cooled to -20°, is added dropwise 1.1 g triethyl amine and then dropwise 1.1 g ethyl chloroformate. The reaction mixture is allowed gradually to come to room temperature and stirred for 2 hours. There is then added 1.0 g triethylamine followed by 1.6 g o-methylphenyl hydrazine hydrochloride and the reaction mixture then stirred for 16 hours. Thereafter the reaction mixture is extracted five times with portions of 2 N hydrochloric acid, then once with 2 N aqueous sodium hydroxide and washed extensively with saturated aqueous sodium chloride. The organic phase is then dried over anh. sodium sulphate, filtered and the filtrate evaporated i.v. to dryness to obtain a residue. The residue is then chromatographed over silica gel, with chloroform as the eluent. The desired fractions** are combined and evaporated i.v. to dryness to yield the title product as a waxy solid, NMR; b +0.65(3), b -0.3(1), d 8.0(1), d 6.1(1), s 2.1(3).

Workup

  1. customto come to room temperature
  2. stirringthe reaction mixture then stirred for 16 hours
  3. extractionThereafter the reaction mixture is extracted five times with portions of 2 N hydrochloric acid
  4. washonce with 2 N aqueous sodium hydroxide and washed extensively with saturated aqueous sodium chloride
  5. dry with materialThe organic phase is then dried over anh. sodium sulphate
  6. filtrationfiltered
  7. customthe filtrate evaporated i.v
  8. customto dryness to obtain a residue
  9. customThe residue is then chromatographed over silica gel, with chloroform as the eluent
  10. customevaporated i.v

Sources & evidence

ORD record
ord-57242f2eaddb4cde868b2be4be49173b
Source dataset
uspto-grants-1980_05
Patent number
US04201785

Reaction notes

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