Trifluoroacetic acid → (2,4-Bis-benzyloxy-5-isopropyl-phenyl)-(5-nitro-1,3-dihydro-isoindol-2-yl)methanone

HRID 425187Notes

Reaction equation

HRID 425187 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:28]([C:39]([CH3:41])=[CH2:40])=[CH:27][C:10]=1[C:11](NC1C=CC(CN2CCOCC2)=CC=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:42]([C:45]1[CH:46]=[C:47]2[C:51](=[CH:52][CH:53]=1)[CH2:50][NH:49][CH2:48]2)([O-:44])=[O:43].C(O)(C(F)(F)F)=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:28]([CH:39]([CH3:41])[CH3:40])=[CH:27][C:10]=1[C:11]([N:49]1[CH2:48][C:47]2[C:51](=[CH:52][CH:53]=[C:45]([N+:42]([O-:44])=[O:43])[CH:46]=2)[CH2:50]1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 64244695-NitroisoindolineHCID 667016982,4-Bis-benzyloxy-5-isopropenyl-N-(4-morpholin-4-ylmethyl-phenyl)-benzamide

Product 1

HCID 66672501(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-(5-nitro-1,3-dihydro-isoindol-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (505 mg; 1.3 mmol) (Preparation B5), 5-nitroisoindoline, TFA (360 mg; 1 equiv.), EDAC (300 mg; 1.2 equiv.), HOBt (210 mg; 1.2 equiv.) and NEt3 (270 μl; 1.5 equiv.) in DMF (10 ml) was stirred at room temperature overnight then evaporated in vacuo The residue was partitioned between EtOAc and 2M HCl, the EtOAc layer was separated, washed with saturated NaHCO3, dried (MgSO4) and evaporated. Purification by flash column chromatography (1:4 then 1:2 then 1:1 EtOAc/P.E. as eluant) gave 460 mg of (2,4-bis-benzyloxy-5-isopropyl-phenyl)-(5-nitro-1,3-dihydro-isoindol-2-yl) methanone. MS: [M+H]+ 328.

Workup

  1. customthen evaporated in vacuo The residue
  2. customwas partitioned between EtOAc and 2M HCl
  3. customthe EtOAc layer was separated
  4. washwashed with saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification by flash column chromatography (1:4

Sources & evidence

ORD record
ord-4584c6fd093b40b891f7a38ca7e3ae4f
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

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