Trifluoroacetic acid → HCID 86753319, compound

HRID 356098Notes

Reaction equation

HRID 356098 reaction equation
ClCl.[SiH](CC)(CC)CC.[C:10]([OH:16])([C:12]([F:15])([F:14])[F:13])=[O:11].C(O)(C(F)(F)F)=O.[NH2:24][C@H:25]([C:28]([OH:30])=[O:29])[CH2:26][SH:27].[NH2:31][C:32]1[CH:48]=[CH:47][C:35]([C:36]([NH:38][C@H:39]([C:44]([OH:46])=[O:45])[CH2:40][CH2:41][S:42][CH3:43])=[O:37])=[CH:34][C:33]=1[CH3:49]>>[NH2:24][C@H:25]([C:28]([OH:30])=[O:29])[CH2:26][SH:27].[OH:16][C:10]([C:12]([F:15])([F:14])[F:13])=[O:11].[NH2:31][C:32]1[C:33]2[C:34](=[CH:26][CH:25]=[CH:28][CH:49]=2)[C:35]([C:36]([NH:38][C@H:39]([C:44]([OH:46])=[O:45])[CH2:40][CH2:41][S:42][CH3:43])=[O:37])=[CH:47][CH:48]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 24526ChlorineHCID 86753320HCID 86753320, compound

Product 1

HCID 86753319HCID 86753319, compound

Procedure

N-BOC-S-trityl-cysteine-4-amino-1-naphthoyl methionine methyl ester (83.3 mg, 0.11 mmol) was taken up in THF (0.7 ml) and to this mixture was added 0.5M LiOH (0.43 ml) at 0° C. The mixture was stirred at 0° C. for 35 minutes. The solvent was removed in vacuo using a cold water bath. The residue was worked up as described for TFA-cysteine-4-amino-3-methylbenzoyl methionine in Example 2, and 74.1 mg of the free acid was obtained. This was then dissolved into CH2 Cl2 (1 ml) and Et3SiH (0.015 ml) was added followed by TFA (1 ml). The reaction mixture was stirred at room temperature for 1 h and worked up as further described for TFA-cysteine-4-amino-3-methylbenzoyl methionine in Example 2. After lyophilization, 42.4 mg of crude material was obtained which was then purified on the HPLC using 0.1% TFA in water and acetonitrile. mp 121°-125° C.; [α]25D =+2.4°(c=0.8, H2O); 1H NMR (CD3OD) 2.03-2.13 (4 H, m), 2.22-2.36 (1 H, m), 2.59-2.74 (2 H, m), 3.16-3.33 (2 H, m), 4.42 (1 H, m), 4.84-4.89 (1 H, m), 7.57-7.61 (2 H, m), 7.64 (1 H, d, J=7.7 Hz), 7.70 (1 H, d, J=7.7 Hz), 8.08-8.11 (1 H, m), 8.29-8.32 (1 H, m), 8.98 (1 H, d, J=7.7 Hz); 13C NMR (CD3OD) 15.19, 26.45, 31.50, 31.63, 53.20, 56.72, 122.52, 123.43, 126.43, 126.12, 127.02, 127.96, 128.32, 129.49, 132.27, 134.15, 135.12, 168.11, 172.41, 175.17; anal. calc. for C21H23F3N3O6S2, C: 47.19, H: 4.34, N: 7.86; found, C: 46.53, H: 4.56, N: 7.59; Note: difference for C is 0.65.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-1f849487f9f841d6a5882fef6ce0c776
Source dataset
uspto-grants-1998_11
Patent number
US05834434

Reaction notes

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