L-(+)-Cysteine → HCID 58329604, compound

HRID 1964170Notes

Reaction equation

HRID 1964170 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:7]([CH:10]=1)[C:8]#[N:9].[OH:16][C:17]1[CH:25]=[CH:24][C:23]2[N:22]3[CH2:26][CH2:27][CH:28]([CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])[C:21]3=[CH:20][C:19]=2[CH:18]=1.C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)CS>CN(C=O)C.C(O)(C(F)(F)F)=O.O>[C:8]([C:7]1[CH:10]=[C:3]([CH:4]=[CH:5][C:6]=1[CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:2][O:16][C:17]1[CH:25]=[CH:24][C:23]2[N:22]3[CH2:26][CH2:27][CH:28]([CH2:29][C:30]([OH:32])=[O:31])[C:21]3=[CH:20][C:19]=2[CH:18]=1)#[N:9]

Participants

8

Reactant 4

HCID 5862L-(+)-CysteineHCID 11430Potassium CarbonateHCID 67249455tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateHCID 67249477HCID 67249477, compound

Product 1

HCID 58329604HCID 58329604, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

5-(Chloromethyl)-2-cyclopentylbenzonitrile (38.2 mg, 0.174 mmol), tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (50 mg, 0.174 mmol), and K2CO3 (36.1 mg, 0.261 mmol) were dissolved in DMF and heated to 60° C. for 16 h. The reaction mixture was filtered through Celite® and purified by HPLC. The intermediate was isolated and dissolved in TFA (0.2M) and added D/L-cysteine. After 15 min, the mixture was poured into water and extracted with DCM. The organic extract was concentrated to give the title compound. LCMS m/z=415.6 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.55-1.67 (m, 2H), 1.70-1.78 (m, 2H), 1.80-1.88 (m, 2H), 2.11-2.20 (m, 2H), 2.26-2.36 (m, 1H), 2.66 (dd, J=16.5, 8.6 Hz, 1H), 2.86-2.97 (m, 2H), 3.42 (quintet, J=8.6 Hz, 1H), 3.75 (quintet, J=7.3 Hz, 1H), 3.97-4.05 (m, 1H), 4.10-4.17 (m, 1H), 5.06 (s, 2H), 6.12 (s, 1H), 6.85 (dd, J=8.0, 2.0 Hz, 1H), 7.06 (d, J=2.0 Hz, 1H), 7.14 (d, J=8.8 Hz, 1H), 7.39 (d, J=8.2 Hz, 1H), 7.60 (d, J=8.3 Hz, 1H), 7.69 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. custompurified by HPLC
  3. customThe intermediate was isolated
  4. extractionextracted with DCM
  5. extractionThe organic extract
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-d6a4506c200544dd908808164d55916e
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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