Diethyl Ether → HCID 69203917, compound

HRID 2378206Notes

Reaction equation

HRID 2378206 reaction equation
[ClH:1].O1CCOCC1.[NH2:8][CH:9]([CH2:37][O:38]C(C)(C)C)[C:10]([NH:12][C:13]1[CH:18]=[C:17]([C:19]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=2)=[CH:20][C:21]#[N:22])[CH:16]=[CH:15][C:14]=1[O:35][CH3:36])=[O:11].CCOCC>C(Cl)Cl>[ClH:1].[NH2:8][CH:9]([CH2:37][OH:38])[C:10]([NH:12][C:13]1[CH:18]=[C:17]([C:19]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=2)=[CH:20][C:21]#[N:22])[CH:16]=[CH:15][C:14]=1[O:35][CH3:36])=[O:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 204431481,4-Dioxane hydrochlorideHCID 69202454HCID 69202454, compound

Product 1

HCID 69203917HCID 69203917, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4N HCl/dioxane (1 mL) was added to a stirred solution of 2-amino-N-{5-[2-cyano-1-(3,4,5-trimethoxy-phenyl)-vinyl]-2-methoxy-phenyl}-3-t-butoxy-propionamide (0.5 g, 1.1 mmol) in CH2Cl2 (10 mL). The resulting mixture was stirred at room temperature for 1 day. Ether (20 mL) was added and the mixture was stirred for 2 h. The slurry was filtered and washed with ether to afford mixture isomers of 2-amino-N-{5-[2-cyano-1-(3,4,5-trimethoxy-phenyl)-vinyl]-2-methoxy-phenyl}-3-hydroxy-propionamide hydrochloride (0.4 g, 78%) as white solid: mp 151-153° C.; 1H NMR (DMSO-d6) δ 9.89 (9.94) (s 1H), 8.31 (b, 3H), 7.98-7.95 (m, 1H), 7.39-7.16 (m, 2H), 6.68 (6.65)-(s, 2H), 6.12 (6.25) (s, 1H), 5.63 (b, 1H), 4.18 (b, 1H), 3.91 (d, J=8 Hz, 2H), 3.87-3.70 (m, 12H); 13C NMR (DMSO-d6) δ 166.20, 161.24 (160.99), 152.62, 151.52 (150.82), 139.43 (138.36), 133.54 (132.24), 129.80 (128.56), 126.60 (126.29), 126.16 (125.31), 122.99 (122.32), 118.51 (118.47), 111.50 (111.16), 106.91 (106.26), 94.46 (93.64), 66.33, 60.33 (60.15), 56.15, 56.02, 54.43; Anal Calcd for C22H26N3O6Cl+0.2H2O: C, 56.52; H, 5.69; N, 8.99; Cl, 7.58. Found: C, 56.29; H, 5.81; N, 8.63; Cl, 7.35.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. filtrationThe slurry was filtered
  3. washwashed with ether

Sources & evidence

ORD record
ord-f4966d41a4714c97bfe9d78ffc818dd5
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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