Glycine methyl ester hydrochloride → Methyl 3-(((5-bromopyridin-2-yl)methoxy)carbonylamino)propanoate

HRID 2175242Notes

Reaction equation

HRID 2175242 reaction equation
CC1C(C)=CC=CC=1OCCCC(N1C2C(=C(C3C=CC(COC(NCC(OC)=O)=O)=CC=3)C=CC=2)CCC1)=O.C(=O)(OC1C=CC([N+]([O-])=O)=CC=1)OCC1C=CC(C2C=CC=C3C=2CCCN3C(=O)CCCOC2C=CC=C(C)C=2C)=CC=1.[C:85](=[O:105])(OC1C=CC([N+]([O-])=O)=CC=1)[O:86][CH2:87][C:88]1[CH:93]=[CH:92][C:91]([Br:94])=[CH:90][N:89]=1.Cl.NCC(OC)=O.Cl.[NH2:114][CH2:115][CH2:116][C:117]([O:119][CH3:120])=[O:118]>>[Br:94][C:91]1[CH:92]=[CH:93][C:88]([CH2:87][O:86][C:85]([NH:114][CH2:115][CH2:116][C:117]([O:119][CH3:120])=[O:118])=[O:105])=[N:89][CH:90]=1

Participants

6

Reactant 5

HCID 122755Glycine methyl ester hydrochlorideHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 70982580Methyl 2-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)acetateHCID 867125814-(1-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyl 4-nitrophenyl carbonateHCID 86712582(5-Bromopyridin-2-yl)methyl 4-nitrophenyl carbonate

Product 1

HCID 70981842Methyl 3-(((5-bromopyridin-2-yl)methoxy)carbonylamino)propanoate

Procedure

The title compound was prepared using a procedure analogous to methyl 2-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)acetate except that 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyl 4-nitrophenyl carbonate was replaced with (5-bromopyridin-2-yl)methyl 4-nitrophenyl carbonate and methyl 2-aminoacetate hydrochloride was replaced with methyl 3-aminopropanoate hydrochloride. LCMS, [M+H]+=317.0.

Sources & evidence

ORD record
ord-222d4b7824b4438c8710be528572698d
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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