Lithium Hydroxide → Cysteine 4-amino-3-methylbenzoyl methionine

HRID 1739149Notes

Reaction equation

HRID 1739149 reaction equation
C([NH:8][C@H:9]([C:31]([OH:33])=[O:32])[CH2:10][S:11]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OC(C)(C)C)=O.C[O:35][C:36](=[O:56])[C@H:37]([CH2:52][CH2:53][S:54][CH3:55])[NH:38][C:39]([C:41]1[C:50]2[C:45](=[CH:46]C=CC=2)[C:44]([NH2:51])=[CH:43][CH:42]=1)=[O:40].[Li+].[OH-]>C1COCC1>[NH2:8][C@H:9]([C:31]([OH:33])=[O:32])[CH2:10][SH:11].[NH2:51][C:44]1[CH:43]=[CH:42][C:41]([C:39]([NH:38][C@H:37]([C:36]([OH:56])=[O:35])[CH2:52][CH2:53][S:54][CH3:55])=[O:40])=[CH:50][C:45]=1[CH3:46]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67566653N-BOC-S-trityl-cysteine 4-amino-1-naphthoyl methionine methyl ester

Product 1

HCID 86754588Cysteine 4-amino-3-methylbenzoyl methionine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

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 0.5 M 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 CH2Cl2 (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 (4H, m), 2.22-2.36 (1H, m), 2.59-2.74 (2H, m), 3.16-3.33 (2H, m), 4.42 (1H, m), 4.84-4.89 (1H, m), 7.57-7.61 (2H, m), 7.64 (1H, d, J=7.7 Hz), 7.70 (1H, d, J=7.7 Hz), 8.08-8.11 (1H, m), 8.29-8.32 (1H, m), 8.98 (1H, 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. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2345dac806cb4d319a1431c3dddfc102
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

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