Hydrochloric Acid → HCID 22504489, compound

HRID 1813929Notes

Reaction equation

HRID 1813929 reaction equation
C(O[CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][N:11]1[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])C1C=CC=CC=1.[CH3:28][N:29](CC1C=CC(C(OCC)=O)=CN=1)[CH3:30].Cl.C(OCC)(=O)C=C>O=[Pt]=O>[CH3:28][N:29]([CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][N:11]1[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 10899819HCID 10899819, compoundHCID 11717794HCID 11717794, compound

Product 1

HCID 22504489HCID 22504489, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

Using the same procedure employed for the preparation of 15c and using 14e (335 mg, 1.6 mmol), 2 M ethereal HCl (6 mL), PtO2 (24 mg), and ethyl acrylate (1.7 mL, 16 mmol) gave 15e (259 mg, 51%) and 17 (52 mg, 12%) following PTLC purification (10% MeOH—CHCl3). Compound 15e: reddish yellow oil; Rf 0.37 (10% MeOH—CHCl3); IR (neat) 2945, 2818, 1731, 1457, 1376, 1182 cm−1; 1H NMR (CDCl3) δ 1.18 (t, J=7.2 Hz, 3H, CH2CH3), 1.19 (t, J=7.2 Hz, 3H, CH2CH3), 1.56-1.70 (m, 4H, C(3)H2, C(4)H2), 2.15 (s, 6H, N(CH3)2), 2.26-2.48 (m, 5H, C(5)H, NCH2CH2, (CH3)2NCH2), 2.69-2.91 (m, 5H, C(2)H, C(6)H2, NCH2CH2), 4.05 (q, J=7.2 Hz, 2H, CH2CH3), 4.07 (q, J=7.2 Hz, 2H, CH2CH3), the 1H NMR assignments were consistent with the COSY spectrum; 13C NMR (CDCl3) 14.0 (CH2CH3), 14.1 (CH2CH3), 22.8 (C(3)), 25.5 (C(4)), 33.5 (NCH2CH2), 40.1 (C(5)), 46.0 (N(CH3)2), 49.3 (C(6)), 49.7 (NCH2CH2), 55.4 (C(2)), 57.7 ((CH3)2NCH2), 60.1 (2C, CH2CH3), 172.6 (C(O)), 174.2 (C(O)) ppm, the assignments were consistent with the DEPT and HMQC spectra; MS (+CI) 315 [M+1]+; Mr (+CI) 315.229 49 [M+1]+ (calcd for C16H31N2O4 315.228 38). Compound 17 (cis- and trans-mixture): Rf 0.75 (10% MeOH—CHCl3); 1H NMR (CDCl3) δ 1.00 (d, J=6.6 Hz, 2H), 1.10 (d, J=6.6 Hz, 1H), 1.21-1.28 (m, 6H), 1.44-2.00 (m, 4H), 2.21-2.30 (m, 1H), 2.42-2.59 (m, 4H), 2.67-2.88 (m, 3H), 4.08-4.17 (m, 4H).

Sources & evidence

ORD record
ord-df865e20a08148bfa588ca9352620fa9
Source dataset
uspto-grants-2005_04
Patent number
US06875774B2

Reaction notes

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