Trifluoroacetic acid → HCID 54380235, compound

HRID 651644Notes

Reaction equation

HRID 651644 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([CH2:21][N:22]3[CH2:26][CH2:25][CH:24]([NH:27]C(OC(C)(C)C)=O)[C:23]3=[O:35])=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.CCN(CC)CC.[Cl:50][C:51]1[CH:52]=[CH:53][C:54]2[CH:58]=[C:57]([S:59](Cl)(=[O:61])=[O:60])[S:56][C:55]=2[CH:63]=1>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([CH2:21][N:22]3[CH2:26][CH2:25][CH:24]([NH:27][S:59]([C:57]4[S:56][C:55]5[CH:63]=[C:51]([Cl:50])[CH:52]=[CH:53][C:54]=5[CH:58]=4)(=[O:61])=[O:60])[C:23]3=[O:35])=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 54386384HCID 54386384, compound

Product 1

HCID 54380235HCID 54380235, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(3-tert-butoxycarbonylamino-2-oxopyrrolidin-1-ylmethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (0.347 g, 0.72 mmol) in 8 mL of CH2Cl2 is added 2 mL of TFA. After 4 hours, the solution is concentrated. The residue is dissolve in CH2Cl2 and Et3N (0.30 mL, 2.17 mmol) and 6-chloro benzo[b]thiophene sulfonyl chloride (0.23 g, 0.87 mmol) are added. After 16 hours, the solution is concentrated. The residue is purified by column chromatography eluting with 10% EtOAc/CH2Cl2. The product (0.25 g, 0.51 mmol) was obtained as a white solid.

Workup

  1. concentrationthe solution is concentrated
  2. dissolutionThe residue is dissolve in CH2Cl2
  3. waitAfter 16 hours
  4. concentrationthe solution is concentrated
  5. customThe residue is purified by column chromatography
  6. washeluting with 10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-b948957a94374628ab2373837a5114b6
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

Loading…