Ethyl bromoacetate → HCID 57780740, compound

HRID 1786038Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

{[3-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)propyl]amino}acetic acid was prepared from (2S,4R)-N-{1-[4-(3-amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide. (2S,4R)-N-{1-[4-(3-amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide (0.036 g, 0.07 mmol) was dissolved in dimethylformamide, ethyl bromoacetate (0.008 mL, 0.07 mmol) and potassium carbonate (0.021 g, 0.14 mmol) were added. The reaction was heated to 50° C. for 17 h. The reaction was concentrated down and purified using 50% ethyl acetate/50% hexane to 100% ethyl acetate.

Workup

concentrationThe reaction was concentrated down
custompurified

Sources & evidence

ORD record: ord-f01ab17bfb7c4adebc2abb8cb0da1863
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

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