Hydrochloric Acid → 2-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methylbutanamido]-6-methylbenzoic acid

HRID 1729242Notes

Reaction equation

HRID 1729242 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][C:8]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([NH:17][C:18](=[O:24])[C@H:19]([CH:21]([CH3:23])[CH3:22])[NH2:20])[CH:11]=[CH:10][CH:9]=1.[CH:25]1[C:37]2[CH:36]([CH2:38][O:39][C:40](Cl)=[O:41])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]=2[CH:28]=[CH:27][CH:26]=1.Cl>O1CCOCC1.O>[CH:25]1[C:37]2[CH:36]([CH2:38][O:39][C:40]([NH:20][C@H:19]([C:18]([NH:17][C:12]3[CH:11]=[CH:10][CH:9]=[C:8]([CH3:7])[C:13]=3[C:14]([OH:16])=[O:15])=[O:24])[CH:21]([CH3:22])[CH3:23])=[O:41])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]=2[CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 541805686-methyl-2-(L-valylamino)benzoic acid

Product 1

HCID 538591852-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methylbutanamido]-6-methylbenzoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

284 mg of sodium carbonate and 336 mg of 6-methyl-2-(L-valylamino)benzoic acid were dissolved in a mixture consisting of 17 ml of 1,4-dioxane and 12 ml of water, followed by adding dropwise a solution of 345 mg of 9-fluorenylmethoxycarbonyl chloride in 7 ml of 1,4-dioxane under ice-cooling. After stirring for 3.5 hours at room temperature, the reaction mixture was poured into water, acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by a silica gel column chromatography (eluting solution: hexane-ethyl acetate-acetic acid) to give 460 mg of 2-{[N-(9-fluorenylmethoxy-carbonyl)-L-valyl]amino}-6-methylbenzoic acid.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by a silica gel column chromatography (eluting solution: hexane-ethyl acetate-acetic acid)

Sources & evidence

ORD record
ord-98f7ba6898274906aafe4bd2ca3c9145
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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