Lithium Hydroxide → 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanine

HRID 1976957Notes

Reaction equation

HRID 1976957 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:49])[C@H:6]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39]([C:41]2[C:46]([Cl:47])=[CH:45][CH:44]=[CH:43][C:42]=2[Cl:48])=[O:40])=[CH:34][CH:33]=1)[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=3)=[N:19][N:18]=[N:17]2)=[CH:12][C:11]=1[Cl:30])=[O:9]>CO.C1COCC1.O>[Cl:47][C:46]1[CH:45]=[CH:44][CH:43]=[C:42]([Cl:48])[C:41]=1[C:39]([NH:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][C@@H:6]([C:5]([OH:49])=[O:4])[NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=4)=[N:19][N:18]=[N:17]3)=[CH:12][C:11]=2[Cl:30])=[O:9])=[CH:37][CH:36]=1)=[O:40]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 698493244-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanine methyl ester

Product 1

HCID 540037814-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanineYield 77.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

An aqueous 1N lithium hydroxide solution (0.33 mL) was added to a solution of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanine methyl ester (75 mg; 0.108 mmol) in methanol (0.66 mL) and THF (0.66 mL) and the mixture was stirred at room temperature for 90 min. After the solvents were stripped under reduced pressure, the residue was dissolved in water (20 mL) and extracted with diethyl ether (3×5 mL). The aqueous layer was filtered through Celite, then acidified with 1 N HCl (0.35 mL). The resulting colorless solid was filtered off, washed with water, and dried in vacuo to give 57 mg of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanine. FAB HRMS: (C31H24Cl3N7O5) Obs. Mass 680.0981 Calcd. Mass 680.0983 (M+H).

Workup

  1. extractionextracted with diethyl ether (3×5 mL)
  2. filtrationThe aqueous layer was filtered through Celite
  3. filtrationThe resulting colorless solid was filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a3fec1f3b0ca418890ecc0347040f6f3
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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