3-Chloroaniline → HCID 10937249, compound

HRID 1376398Notes

Reaction equation

HRID 1376398 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][C:14](=[O:16])[C@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 79323-ChloroanilineHCID 89857Boc-L-methionine

Product 1

HCID 10937249HCID 10937249, compound

Procedure

Coupling of N-tert-butoxycarbonyl-L-methionine (1a) and 3-chloroaniline (2c) according to General Procedure A, gave after purification on a SILICA GEL column hexane-acetone (3:1) an oily liquid of (3c) (C16H23N2O3S1Cl1, 94%), Rf=0.40 (hexane-acetone 3:1), [α]D23 =-36.8° (c 1.44, CHCl3), IR (KBr) ν: 440, 461, 519, 548, 606, 681, 739, 777, 864, 880, 903, 963, 999, 1026, 1049, 1076, 1099, 1165, 1252, 1267, 1300, 1368, 1393, 1427, 1456, 1483, 1506, 1522, 1539, 1595, 1670, 1684, 1697, 2336, 2361, 2868, 2918, 2978, 3061, 3086, 3131, 3198, 3291, 3522, 3545 cm-1, 1H NMR (CDCl3) δ: 8.472 (br s, 1H, Ar--NH), 7.616-7.629 (m, 1H, ArH), 7.240-7.283 (m, 1H, ArH), 7.153 (dd, 1H, J 7.8 Hz and 8.1 Hz, ArH), 7.023 (d, 1H, J 7.8 Hz, ArH), 5.377 (br s, 1H, NH), 4.407-4.427 (m, 1H, Hα), 2.566-2.618 (m, 2H, CH2γ), 2.116-2.184 (m, 1H, Hβ), 2.084 (s, 3H, CH3ε), 1.940-2.070 (m, 1H, Hβ), 1.425 (s, 9H, t-Bu); EIMS (70 eV) m/z (%): 358 (M+, 2).

Workup

  1. customgave
  2. customafter purification on a SILICA GEL column hexane-acetone (3:1) an oily liquid of (3c) (C16H23N2O3S1Cl1, 94%), Rf=0.40 (hexane-acetone 3:1), [α]D23 =-36.8° (c 1.44, CHCl3), IR (KBr) ν

Sources & evidence

ORD record
ord-5f3f126dbea8469da58a6b77b50d7c08
Source dataset
uspto-grants-1997_09
Patent number
US05663149

Reaction notes

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