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

HRID 1739135
Notes
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Reaction equation

HRID 1739135 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 67601241
N-BOC-S-trityl-cysteine 4-amino-3-methoxybenzoyl methionine methyl ester
Yield 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 (9H, s), 2.05-2.33 (5H, m), 2.57-2.65 (2H, m), 2.68-2.72 (1H, m), 2.75-2.96 (1H, m), 3.78 (3H, s), 3.84 (3H, s), 4.90-5.00 (1H, m), 5.03-5.18 (1H, m), 7.17-7.48 (17H, m), 8.30-8.38 (1H, m), 8.65 (1H, 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-f31e4982a1604037b237fb8d839e0176
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05965539

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes