1-Hydroxybenzotriazole → HCID 59038461, compound

HRID 1058385Notes

Reaction equation

HRID 1058385 reaction equation
ON1C2C=CC=CC=2N=N1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[C:21]([O:23][CH3:24])=[O:22])[C:15]([OH:17])=O.[C:25]1([C@H:35]([NH2:37])[CH3:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>CN(C)C=O>[CH3:24][O:23][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:14]([C:15]([NH:37][C@@H:35]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=[CH:27][CH:26]=2)[CH3:36])=[O:17])=[CH:13][C:12]=1[Cl:11]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 143722353-Chloro-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 59038461HCID 59038461, compoundYield 116.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-dicyclohexylcarbodiimide (5.12 g, 24.84 mmol) and 1-hydroxybenzotriazole (3.08 g, 24.84 mol) were added to a solution of 3-chloro-4-(methoxycarbonyl)benzoic acid (Example 72; 5.0 g, 23.7 mmol) and (R)-(+)-1-(naphthalen-1-yl)ethylamine (3.45 g, 20.7 mmol) in N,N-dimethylformamide (10 mL). The solution was stirred for 6 h at room temperature, then after the volatiles were removed in vacuo, the residual material was partitioned between ethyl acetate and water. The separated aqueous phase was extracted with three portions of ethyl acetate , then the combined ethyl acetate layers were washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The resulting colorless solid was crystallized from dichloromethane/hexane to yield 8.85 g of (R)-2-chloro-4-[[1-(naphthalen-1-yl)ethylamino]carbonyl]benzoic acid methyl ester (over theory; material 94% pure by analytical HPLC).

Workup

  1. customafter the volatiles were removed in vacuo
  2. customthe residual material was partitioned between ethyl acetate and water
  3. extractionThe separated aqueous phase was extracted with three portions of ethyl acetate
  4. washthe combined ethyl acetate layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe resulting colorless solid was crystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-640e30e47f7b48c0b7e06ce6a4b97801
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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