HCID 58532552, compound → HCID 53241557, compound

HRID 2069022Notes

Reaction equation

HRID 2069022 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:47])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]([C@@H:34]4[CH2:39][O:38][CH2:37][CH2:36][N:35]4C(OC(C)(C)C)=O)=[O:33])[CH:26]=3)=[CH:15][CH:14]=2)[N:7]([C:48]2[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:47])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]([C@@H:34]4[CH2:39][O:38][CH2:37][CH2:36][NH:35]4)=[O:33])[CH:26]=3)=[CH:15][CH:14]=2)[N:7]([C:48]2[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 58532552HCID 58532552, compound

Product 1

HCID 53241557HCID 53241557, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of the carbamate (9) (30 mg, 0.04 mmol) in DCM/TFA (1:1 v/v, 2.0 mL) was stirred at RT for 1 hr and was then evaporated in vacuo. the resulting residue was subjected to capture and release on SCX and then triturated from DCM (5.0 mL) and isohexane (5.0 mL) to afford the title compound (Example 11) as a brown solid (15 mg, 63%): m/z 634 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 1.26 (9H, s), 2.39 (3H, s), 2.73-2.92 (3H, overlapping m), 3.56-3.64 (4H, overlapping m), 3.82 (1H, m), 5.38 (2H, s), 6.34 (1H, s), 7.00 (1H, d), 7.29 (1H, dd), 7.35 (2H, m), 7.42 (2H, m), 7.55-7.62 (3H, overlapping m), 7.91 (1H, m), 8.30 (1H, dd), 8.32 (1H, br s), 8.35 (1H, dd), 8.56 (1H, br s), 8.77 (1H, br s) 10.16 (1H, br s).

Workup

  1. customwas then evaporated in vacuo
  2. customtriturated from DCM (5.0 mL) and isohexane (5.0 mL)

Sources & evidence

ORD record
ord-a92693989d614037816646cee3e8ae89
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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