3-Acetoxy-2-methylbenzoic acid → HCID 16072569, compound

HRID 1838085Notes

Reaction equation

HRID 1838085 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:34])=[C:6]([CH:33]=1)[CH2:7][NH:8][C:9]([C@@H:11]1[C:15]([CH3:17])([CH3:16])[S:14][CH2:13][N:12]1[C:18](=[O:32])[C@@H:19]([OH:31])[C@@H:20]([NH2:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:10].C([O:38][C:39]1[C:40]([CH3:48])=[C:41]([CH:45]=[CH:46][CH:47]=1)[C:42](O)=[O:43])(=O)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:34])=[C:6]([CH:33]=1)[CH2:7][NH:8][C:9]([C@@H:11]1[C:15]([CH3:17])([CH3:16])[S:14][CH2:13][N:12]1[C:18](=[O:32])[C@@H:19]([OH:31])[C@@H:20]([NH:30][C:42](=[O:43])[C:41]1[CH:45]=[CH:46][CH:47]=[C:39]([OH:38])[C:40]=1[CH3:48])[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)=[O:10]

Participants

3

Reactant 2

HCID 37985573-Acetoxy-2-methylbenzoic acidHCID 69879800HCID 69879800, compound

Product 1

HCID 16072569HCID 16072569, compoundYield 81%

Procedure

The reaction was carried out in the same manner as in Step 3 of Example 1 using the compound obtained in Step 2 (150 mg) and 3-acetoxy-2-methylbenzoic acid (53 mg). The resulting crude product was purified by silica gel column chromatography (CH2Cl2—MeOH) and reprecipitated from n-hexane to obtain the target compound (125 mg, 81%).

Workup

  1. customThe resulting crude product was purified by silica gel column chromatography (CH2Cl2—MeOH)
  2. customreprecipitated from n-hexane

Sources & evidence

ORD record
ord-d911395cacf8424eac2053663fb9f544
Source dataset
uspto-grants-2004_01
Patent number
US06673772B2

Reaction notes

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