Triethylamine → N-BOC-S-trityl-cysteine 4-amino-3-methoxybenzoyl methionine methyl ester

HRID 356083Notes

Reaction equation

HRID 356083 reaction equation
[C:1]([NH:8][C@H:9]([C:31]([OH:33])=[O:32])[CH2:10][S:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.Cl.[CH3:42][O:43][C:44](=[O:62])[C@H:45]([CH2:58][CH2:59][S:60][CH3:61])[NH:46][C:47](=[O:57])[C:48]1[CH:53]=[CH:52][C:51]([NH2:54])=[C:50]([O:55][CH3:56])[CH:49]=1.C(N[C@H](C(O)=O)CSC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OC(C)(C)C)=O.COC(=O)[C@H](CCSC)NC(=O)C1C=CC(N)=CC=1>C1COCC1.C(Cl)Cl>[C:1]([NH:8][C@H:9]([C:31]([OH:33])=[O:32])[CH2:10][S:11][C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:42][O:43][C:44](=[O:62])[C@H:45]([CH2:58][CH2:59][S:60][CH3:61])[NH:46][C:47](=[O:57])[C:48]1[CH:53]=[CH:52][C:51]([NH2:54])=[C:50]([O:55][CH3:56])[CH:49]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 11167161N-((1,1-Dimethylethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteineHCID 67565269N-BOC-S-trityl-cysteine 4-aminobenzoyl methionine methyl esterHCID 67566236HCl 4-amino-3-methoxybenzoyl methionine methyl ester

Product 1

HCID 67601241N-BOC-S-trityl-cysteine 4-amino-3-methoxybenzoyl methionine methyl esterYield 15.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-BOC-S-trityl-cysteine (0.76 g, 1.74 mmol) in dry THF (27.5 ml) was reacted with Et3N (0.24 ml), IBCF (0.23 ml, 1.74 mmol) at -10° C. as described above. HCl-4-amino-3-methoxybenzoyl methionine methyl ester (0.55 g, 1.58 mmol) in dry CH2Cl2 (8.7 ml) with Et3N (0.30 ml) was added to the mixture and was allowed to stir overnight under nitrogen. It was worked up as described for N-BOC-S-trityl-cysteine-4-aminobenzoyl methionine methyl ester in Example 1, and the crude material was chromatographed on silica gel using a 2:1 mixture of hexanes and ethyl acetate to give 0.18 g (15.2%) of pure product. 1H NMR (CDCl3) 1.45 (9 H, s), 2.05-2.33 (5 H, m), 2.57-2.65 (2 H, m), 2.68-2.72 (1 H, m), 2.75-2.96 (1 H, m), 3.78 (3 H, s), 3.84 (3 H, s), 4.90-5.00 (1 H, m), 5.03-5.18 (1 H, m), 7.17-7.48 (17 H, m), 8.30-8.38 (1 H, m), 8.65 (1 H, br s).

Workup

  1. customthe crude material was chromatographed on silica gel using
  2. additiona 2:1 mixture of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-b6c98498f04f4bc9948f88a0116f0de7
Source dataset
uspto-grants-1998_11
Patent number
US05834434

Reaction notes

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