HCID 18762443, compound → Phenyl carbamate
Reaction equation
[N:1]1([C:10]([O-])=[O:11])C2C(=CC=CC=2)CC1.CCCCCCCCCCS[C:24]1[C:29](=O)[CH2:28][C:27](C)(C)[C@@:26]([OH:41])(/C=C/C(/C)=C\C(O)=O)[C:25]=1C>>[C:10](=[O:11])([O:41][C:26]1[CH:25]=[CH:24][CH:29]=[CH:28][CH:27]=1)[NH2:1]Participants
Procedure
tert-Butyl-2-(1-(4-dimethylamino)phenyl)-1H-imidazole-2-carbonyl)indoline-1-carboxylate (white solid) represented by the following formula (as10) was obtained in the same manner as in Example 1-15, except that tert-butyl-2-(3-oxo-3-(1-(4-dimethylamino)phenyl)-1H-imidazol-2-yl)propyl)phenyl carbamate (an10) obtained in Synthesis Example 14 was used as a substrate in an amount of 21.7 mg (0.05 mmol), the compound represented by the general formula (25) wherein R5 is the functional group F was used as a quaternary ammonium salt in an amount of 6.4 mg (0.005 mmol), and the reaction time was changed to 5 hours. The yield was 88%, and the enantioselectivity determined by HPLC measurement (chiral column: “DAICEL CHIRALPAK IA”, eluant: hexane/ethanol (=10/1), flow rate: 1 mL/min, t1=16 min, t2=24 min) was 78% ee (see Table 1-5). The analysis data for the resulting compound (as10) is shown below.
Sources & evidence
- ORD record
- ord-9c92ce13156b43aebe708d5c24696acb
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018394B2
Reaction notes
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