Dichloromethane → N-BOC-S-trityl-cysteine 4-amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester

HRID 1739145Notes

Reaction equation

HRID 1739145 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=1.C(Cl)Cl.CCN(CC)CC.[C:38]([NH:45][C@H:46]([C:68]([OH:70])=[O:69])[CH2:47][S:48][C:49]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].COC(=O)[C@H](CCSC)NC(=O)C1C=CC(N)=CC=1>C1COCC1>[C:38]([NH:45][C@H:46]([C:68]([OH:70])=[O:69])[CH2:47][S:48][C:49]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]1[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[CH:19]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 186667574-Amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl esterHCID 67565269N-BOC-S-trityl-cysteine 4-aminobenzoyl methionine methyl ester

Product 1

HCID 67601032N-BOC-S-trityl-cysteine 4-amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl esterYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester (0.10 g, 0.26 mmol) was dissolved into dry CH2Cl2 (1.4 ml) and it was allowed to stand. In another flask, N-BOC-S-trityl-Cys (0.12 g, 0.26 mmol) was dissolved into THF (4.4 ml) and was reacted with IBCF (0.03 ml) and Et3N (0.04 ml) as described above. The product was worked up as described for N-BOC-S-trityl-cysteine-4-aminobenzoyl methionine methyl ester in Example 1 and chromatographed on silica gel using a 1:1 hexanes and ethyl acetate elution mixture to give 0.12 g (56.0%) of pure material. 1H NMR (CDCl3) 1.33 (9H, s), 1.61-1.68 (1H, m), 1.73-1.91 (4H, m), 1.96 (2H, t, J=7.6 Hz), 2.24 (6H, s), 2.57-2.64 (2H, m), 3.57 (3H, s), 4.00 (1H, br s), 4.54-4.58 (1H, m), 5.84 (1H, d, J=7.8 Hz), 5.97 (1H, br d), 6.90 (1H, s) , 6.92 (2H, s) , 7.18-7.22 (9H, m), 7.27-7.40 (7H, m), 7.55 (1H, m), 7.61 (1H, m), 8.58 (1H, br s); 13C NMR (CDCl3) 15.11, 21.20, 27.79, 29.25, 31.28, 51.70, 52.28, 54.08, 60.32, 71.45, 80.75, 118.01, 120.80, 126.38, 126.82, 127.98, 129.41, 129.87, 130.22, 138.11, 139.18, 139.79, 141.06, 144.17, 168.38, 169.04, 171.82.

Workup

  1. customchromatographed on silica gel using
  2. washa 1:1 hexanes and ethyl acetate elution mixture

Sources & evidence

ORD record
ord-6395b33658a94446b65bbb8b7d524791
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

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