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Hydrochloric Acid → N-BOC-S-trityl-cysteine 4-amino-1-naphthoyl methionine methyl ester

HRID 356097
Notes
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Reaction equation

HRID 356097 reaction equation
CCN(CC)CC.Cl.[CH3:9][O:10][C:11](=[O:31])[C@H:12]([CH2:27][CH2:28][S:29][CH3:30])[NH:13][C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:26])=[CH:18][CH:17]=1)=[O:15].[C:32]([NH:39][C@H:40]([C:62]([OH:64])=[O:63])[CH2:41][S:42][C:43]([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)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].COC(=O)[C@H](CCSC)NC(=O)C1C=CC(N)=CC=1>C1COCC1.C(Cl)Cl>[C:32]([NH:39][C@H:40]([C:62]([OH:64])=[O:63])[CH2:41][S:42][C:43]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=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:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[CH3:9][O:10][C:11](=[O:31])[C@H:12]([CH2:27][CH2:28][S:29][CH3:30])[NH:13][C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:26])=[CH:18][CH:17]=1)=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 537463294-Amino-1-naphthoyl methionine methyl esterHCID 67565269N-BOC-S-trityl-cysteine 4-aminobenzoyl methionine methyl ester

Product 1

HCID 67566653N-BOC-S-trityl-cysteine 4-amino-1-naphthoyl methionine methyl esterYield 37.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-BOC-S-trityl-Cys (0.31 g, 0.67 mmol) in dry THF (11.2 ml) was reacted with Et3N (0.10 ml) and IBCF (0.10 ml, 0.74 mmol) at -10° C. as described above. HCl.4-amino-1-naphthoyl methionine methyl ester (0.25 g, 0.67 mmol) in dry CH2Cl2 (3.5 ml) was added and the mixture was stirred overnight under nitrogen. The mixture 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 0.20g (37.5 %) of pure product. 1H NMR (CDCl3) 1.48 (9 H, s), 2.10-2.20 (4 H, m), 2.30-2.37 (1 H, m), 2.63 (2 H, t, J=7.4), 2.74 (1 H, J=12.9 Hz, J=5.3 Hz), 2.90 (1 H, J=12.9 Hz, 6.2 Hz), 3.81 (3 H, s), 4.96-5.03 (2 H, m), 6.77 (1 H, d, J=8.0 Hz), 7.18-7.33 (11 H, m), 7.44-7.56 (7 H, m), 7.60 (1 H, d, J=7.7 Hz), 7.88 (1 H, d, J=8.0 Hz), 8.00 (1 H, d, J=7.1 Hz), 8.37 (1 H, d, J=8.4 Hz), 8.94 (1 H, br s); 13C NMR (CDCl3) 15.23, 26.52, 31.41, 31.50, 52.98, 53.31, 56.79, 68.15, 122.52, 123.54, 126.16, 126.99, 128.03, 128.39, 129.52, 132.30, 134.04, 135.24, 168.08, 172.38, 173.94.

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-3b41ded45bcb441c943ff4ca83af8f85
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05834434

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes