Trifluoroacetic acid → 7-amino-4-(3,4-dihydroxycyclopentyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one trifluoroacetate

HRID 511489Notes

Reaction equation

HRID 511489 reaction equation
[OH:1][CH:2]1[CH:6]([OH:7])[CH2:5][CH:4]([C:8]2[CH:9]=[CH:10][C:11]([NH:19]C(=O)OC(C)(C)C)=[C:12]3[C:16]=2[CH2:15][N:14]([CH3:17])[C:13]3=[O:18])[CH2:3]1.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(Cl)Cl>[F:30][C:29]([F:32])([F:31])[C:27]([OH:33])=[O:28].[NH2:19][C:11]1[CH:10]=[CH:9][C:8]([CH:4]2[CH2:3][CH:2]([OH:1])[CH:6]([OH:7])[CH2:5]2)=[C:16]2[C:12]=1[C:13](=[O:18])[N:14]([CH3:17])[CH2:15]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695307tert-butyl[7-(3,4-dihydroxycyclopentyl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate2×

Product 1

HCID 672550847-amino-4-(3,4-dihydroxycyclopentyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [7-(3,4-dihydroxycyclopentyl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate (Compound 243B, 36 mg, 0.099 mmol) in DCM (2 mL) was added TFA (1 mL). The resulting mixture was stirred at rt for 30 min, then evaporated under reduced pressure to give the desired product. This TFA salt was directly used in next step. MS (ES+): m/z=263.09 [MH+]. HPLC: tR=0.78 min (ZQ3, polar—5 min).

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b8c0fececcb94206a2c40835b157621b
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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