Lithium Hydroxide → HCID 71817936, compound

HRID 1478636Notes

Reaction equation

HRID 1478636 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:27])[NH:10][C@@H:11]([CH2:21][C:22]2[N:23]=[CH:24][S:25][CH:26]=2)[C:12](=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:7]1)=[O:5])C.[Li+].[OH-]>C1COCC1.CO.O>[O:20]=[C:12]([NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C@@H:11]([NH:10][C:9]([C@H:8]1[O:7][C@@H:6]1[C:4]([OH:5])=[O:3])=[O:27])[CH2:21][C:22]1[N:23]=[CH:24][S:25][CH:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71818386HCID 71818386, compound

Product 1

HCID 71817936HCID 71817936, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 19a (112 mg, 0.28 mmol); LiOH (6.9 mg, 0.29 mmol); THF/MeOH/H2O (2.5 mL: 1.0 mL: 1.0 mL); yielded 32 as a white solid (45 mg, 43.3%). 1H NMR (MeOD-d4, 400 MHz): δ 8.97 (s, 1H); 7.52-7.50 (d, 2H); 7.32 (s, 1H); 7.30-7.26 (t, 3H); 4.94-4.92 (t, 1H): 3.62 (s, 1H); 3.52-3.45 (q, 2H); 3.43 (s, 1H). 13C NMR (DMSO-d6, 100 MHz): 172.48, 169.65, 168.87, 153.83, 152.41, 138.16, 128.33, 124.04, 120.73, 115.89, 54.49, 53.60, 52.89 32.87. ESI-HRMS (m/z): [M+H+] calcd. for C16H15N3O5S: 360.0660, observed: 360.0673; HPLC method 2: Rt=16.4 min; Purity: 95.2%.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-331642d2697b431fa36e5c5cd5d53b31
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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