Benzoic acid, 4-(acetyloxy)- → 4-(2-(tert-Butoxycarbonylamino)-5-(3-oxocyclopent-1-enyl)phenylcarbamoyl)phenyl acetate

HRID 1907739Notes

Reaction equation

HRID 1907739 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=2)[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].CN(C)[C@@H]1CCN(CC2C=CC(C(O)=O)=CC=2)C1.[C:40]([O:43][C:44]1[CH:52]=[CH:51][C:47]([C:48](O)=[O:49])=[CH:46][CH:45]=1)(=[O:42])[CH3:41]>CCOC(C)=O>[C:40]([O:43][C:44]1[CH:52]=[CH:51][C:47]([C:48](=[O:49])[NH:1][C:2]2[CH:7]=[C:6]([C:8]3[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=3)[CH:5]=[CH:4][C:3]=2[NH:14][C:15]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:21])=[CH:46][CH:45]=1)(=[O:42])[CH3:41]

Participants

5

Reactant 3

HCID 16865Benzoic acid, 4-(acetyloxy)-HCID 59737509(R)-4-((3-(Dimethylamino)pyrrolidin-1-yl)methyl)benzoic acidHCID 59737590tert-Butyl 2-amino-4-(3-oxocyclopent-1-enyl)phenylcarbamate

Product 1

HCID 597372074-(2-(tert-Butoxycarbonylamino)-5-(3-oxocyclopent-1-enyl)phenylcarbamoyl)phenyl acetateYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the same procedure as described in Example 1, step 6 (scheme 1), but substituting compound 4 for compound 258 and compound 7 for 4-acetoxybenzoic acid, title compound 259 was obtained as a yellow oil in 30% yield [after flash chromatography (eluent: 30% AcOEt in hexanes)].

Sources & evidence

ORD record
ord-a748e2e81107472e93512be78f086a1c
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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