Triethylamine → HCID 59608436, compound

HRID 2067158Notes

Reaction equation

HRID 2067158 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.[CH3:19][C:20]([CH3:25])([CH3:24])[C:21](Cl)=[O:22].Cl.[NH2:27][CH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:21](=[O:22])[C:20]([CH3:25])([CH3:24])[CH3:19])=[CH:7][C:3]=1[C:4]([NH:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=1)=[O:6]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 4582102-Chloro-5-hydroxybenzoic acidHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochloride

Product 1

HCID 59608436HCID 59608436, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-chloro-5-hydroxybenzoic acid (1.0 g, 5.8 mmol) in DCM (10 ml) was treated with triethylamine (2.5 eq, 2.0 ml, 14.5 mmol) and 2,2-dimethylpropanoyl chloride (2.0 eq, 1.43 ml, 11.6 mmol). Mixture stirred at room temperature for 2 hours. A solution of methyl 4-(aminomethyl)benzoate hydrochloride (1.5 eq, 1.75 g, 8.7 mmol) and triethylamine (2.0 eq, 1.6 ml, 11.6 mmol) in DCM (10 ml) was then added and the mixture stirred at room temperature for another 2 hours. The mixture was diluted with DCM (300 ml) and aqueous sodium bicarbonate (100 ml), layers separated and aqueous layer extracted again with DCM (200 ml). Organic layers combined, washed with brine, dried over magnesium sulphate and evaporated. Residue purified by column chromatography (Biotage SP4) eluting with 0-30% EtOAc in Hex to give the title compound as a white solid. MS (ES+) m/z 404 [M+H]+ (C21H2235ClNO5). 1H-NMR (400 MHz, d6-DMSO) δ 1.30 (9H, s), 3.85 (3H, s), 4.51 (2H, d, J 6), 7.24 (1H, dd, J 8.8, J 2.8), 7.29 (1H, d, J 2.8), 7.51 (2H, d, J 8.8), 7.56 (2H, d, J 8.4), 7.95 (2H, m).

Workup

  1. stirringthe mixture stirred at room temperature for another 2 hours
  2. customseparated
  3. extractionaqueous layer extracted again with DCM (200 ml)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customResidue purified by column chromatography (Biotage SP4)
  8. washeluting with 0-30% EtOAc in Hex

Sources & evidence

ORD record
ord-4ad1607691d6440ebb9ad9fa63890fcf
Source dataset
uspto-grants-2012_10
Patent number
US08293798B2

Reaction notes

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