Glycine methyl ester hydrochloride → HCID 70982485, compound

HRID 2175274Notes

Reaction equation

HRID 2175274 reaction equation
CO[C:3](=[O:8])[CH2:4][C:5]([OH:7])=[O:6].Cl.NCC(OC)=O.[N:16]1([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]3[CH:41]=[CH:40][CH:39]=[C:38]4[C:33]=3[CH2:34][CH2:35][CH2:36][N:37]4[C:42](=[O:55])[CH2:43][CH2:44][CH2:45][O:46][C:47]3[CH:52]=[CH:51][CH:50]=[C:49]([CH3:53])[C:48]=3[CH3:54])[CH:27]=2)=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[CH3:54][C:48]1[C:49]([CH3:53])=[CH:50][CH:51]=[CH:52][C:47]=1[O:46][CH2:45][CH2:44][CH2:43][C:42]([N:37]1[C:38]2[C:33](=[C:32]([C:28]3[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=3)[CH2:25][O:24][C:22]([N:16]3[CH2:21][CH2:20][N:19]([C:3](=[O:8])[CH2:4][C:5]([OH:7])=[O:6])[CH2:18][CH2:17]3)=[O:23])[CH:41]=[CH:40][CH:39]=2)[CH2:34][CH2:35][CH2:36]1)=[O:55]

Participants

4

Reactant 3

HCID 122755Glycine methyl ester hydrochlorideHCID 5383663-Methoxy-3-oxopropanoic acidHCID 70982584HCID 70982584, compound

Product 1

HCID 70982485HCID 70982485, compound

Procedure

Example 128 was prepared using a procedure analogous to Example 126 except that Example 1 was replaced with 3-methoxy-3-oxopropanoic acid and methyl 2-aminoacetate hydrochloride was replaced with 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyl piperazine-1-carboxylate. LCMS, [M+H]+=628.3. 1H NMR (400 MHz, MeOD) δ 7.54-7.42 (m, 2H), 7.41-7.31 (m, 2H), 7.30-7.14 (m, 3H), 7.06 (t, J=7.9 Hz, 1H), 6.79 (d, J=7.5 Hz, 1H), 6.75 (d, J=8.1 Hz, 1H), 5.25 (s, 2H), 3.97 (br, s, 2H), 3.83 (t, J=7.0 Hz, 2H), 3.74-3.55 (m, 8H), 2.90 (t, J=6.9 Hz, 2H), 2.46 (br. s, 2H), 2.31-2.16 (m, 5H), 1.91 (s, 3H), 1.85 (dt, J=13.3, 6.8 Hz, 2H), 1.37 (s, 2H). HPLC-1: Rt=10.8 min, purity=95.0%; HPLC-2: Rt=10.9 min, purity=93.1%.

Workup

  1. customExample 128 was prepared

Sources & evidence

ORD record
ord-0e22e13038b14f9f8f8f4c759350c0c2
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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