Acetyl chloride → HCID 57699880, compound

HRID 1686012Notes

Reaction equation

[CH:1]1([O:6][C:7](=[O:41])[C@@H:8]([NH2:40])[CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([O:22][C:23]4[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:37])[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:25][CH:24]=4)=[CH:17][CH:18]=[N:19]3)=[CH:14][C:13]=2[O:38][CH3:39])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:42](Cl)(=[O:44])[CH3:43].C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([O:6][C:7](=[O:41])[C@@H:8]([NH:40][C:42](=[O:44])[CH3:43])[CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([O:22][C:23]4[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:37])[C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:25][CH:24]=4)=[CH:17][CH:18]=[N:19]3)=[CH:14][C:13]=2[O:38][CH3:39])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To (S)-2-Amino-4-[4-(4-benzoylamino-phenoxy)-6-methoxy-quinolin-7-yloxy]-butyric acid cyclopentyl ester (120 mg, 0.216 mmol) in DCM (2 ml) were added acetyl chloride (15 μL, 0.216 mmol) and triethylamine (33 μL, 0.238 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 min. then at room temperature for 1 hour. The crude mixture was concentrated under vacuum and purified by preparative HPLC to provide the title compound as a mono-TFA salt (67 mg, 52% yield).

Workup

waitat room temperature for 1 hour
concentrationThe crude mixture was concentrated under vacuum
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-a153173dbfca4b4b85cd052157cca82f
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148531B2

Reaction notes

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