Dichloromethane → HCID 71237041, compound

HRID 1045792Notes

Reaction equation

HRID 1045792 reaction equation
FC(F)(F)C(O)=O.[Si]([O:15][CH2:16][CH2:17][N:18]1[C:24]2[N:25]=[CH:26][CH:27]=[CH:28][C:23]=2[C:22]2[CH:29]=[CH:30][CH:31]=[CH:32][C:21]=2[CH:20]([NH:33][C:34](=[O:45])[C@@H:35]([NH:37]C(=O)OC(C)(C)C)[CH3:36])[C:19]1=[O:46])(C(C)(C)C)(C)C.ClCCl>CO>[NH2:37][C@@H:35]([CH3:36])[C:34]([NH:33][CH:20]1[C:21]2[CH:32]=[CH:31][CH:30]=[CH:29][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[N:25][C:24]=2[N:18]([CH2:17][CH2:16][OH:15])[C:19]1=[O:46])=[O:45]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 71237441HCID 71237441, compound

Product 1

HCID 71237041HCID 71237041, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add trifluoroacetic acid (30 mL, 396.76 mmol) over 5 minutes to a 0° C. solution of tert-butyl N-[(1S)-2-[[5-[2-(tert-butyl(dimethyl)silyl)oxyethyl]-6-oxo-7H-pyrido[2,3-d][3]benzazepin-7-yl]amino]-1-methyl-2-oxo-ethyl]carbamate (5.56 g, 10.0 mmol) and dichloromethane (30 mL) and allow to warm and stir at ambient temperature for 5 hours. Purify the residue by flash chromatography via SCX® columns (Isolute SCX-2×6) eluting with methanol followed by ethyl acetate: methanol (2N ammonia) (1:1) to obtain the title compound as a white solid (3.48 g, 10.2 mmol) in quantitative yield. MS (m/z): 341 (M+1).

Workup

  1. temperatureto warm
  2. customPurify the residue by flash chromatography via SCX® columns (Isolute SCX-2×6)
  3. washeluting with methanol

Sources & evidence

ORD record
ord-50f29f9d58d14d149c225e0481116191
Source dataset
uspto-grants-2013_10
Patent number
US08569286B2

Reaction notes

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