2-Chloroaniline → HCID 11057461, compound

HRID 1376397Notes

Reaction equation

HRID 1376397 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:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>>[Cl:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][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]

Participants

3

Reactant 2

HCID 72402-ChloroanilineHCID 89857Boc-L-methionine

Product 1

HCID 11057461HCID 11057461, compound

Procedure

Reaction of N-tert-butoxycarbonyl-L-methionine (1a) and 2-chloroaniline (2b) according to General Procedure A, gave after purification on a SILICA GEL column with hexane-acetone (3:1) as the eluent, an oily liquid of (3b) (C16H23N2O3S1Cl1, 79%), Rf=0.43 (hexane-acetone 3:1), [α]D23 =-41.5° (c 0.65, CHCl3), IR (KBr) ν: 536, 548, 606, 648, 667, 691, 752, 864, 963, 1036, 1055, 1165, 1250, 1298, 1368, 1393, 1441, 1524, 1593, 1616, 1684, 1696, 2338, 2361, 2870, 2920, 2978, 3036, 3061, 3121, 3314 cm-1, 1H NMR (CDCl3) δ: 8.551 (s, 1H, Ar--NH), 8.321-8.355 (m, 1H, ArH), 7.334-7.336 (m, 1H, ArH), 7.221-7.279 (m, 1H, ArH), 7.005-7.062 (m, 1H, ArH), 5.194-5.214 (br s, 1H, NH), 4.442-4.462 (m, 1H, Hα), 2.590-2.638 (m, 2H, CH2γ), 2.144-2.281 (m, 1H, Hβ), 2.112 (s, 3H, CH3ε), 1.966-2.112 (m, 1H, Hβ), 1.44 (s, 9H, t-Bu); EIMS (70 eV) m/z (%): 358 (M+, 2).

Workup

  1. customgave
  2. customafter purification on a SILICA GEL column with hexane-acetone (3:1) as the eluent
  3. customan oily liquid of (3b) (C16H23N2O3S1Cl1, 79%), Rf=0.43 (hexane-acetone 3:1), [α]D23 =-41.5° (c 0.65, CHCl3), IR (KBr) ν

Sources & evidence

ORD record
ord-200ca5ea9599429d8adc2cfac47d94ff
Source dataset
uspto-grants-1997_09
Patent number
US05663149

Reaction notes

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