Hydrochloric Acid → HCID 70048380, compound

HRID 1768914Notes

Reaction equation

HRID 1768914 reaction equation
[ClH:1].C([O:6][C:7](=[O:33])[C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:32])[CH2:14][NH:15][S:16]([C:19]1[C:28]2[C:23](=[C:24]([N:29]([CH3:31])[CH3:30])[CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])(C)(C)C.CCOCC>O1CCOCC1>[ClH:1].[CH3:30][N:29]([CH3:31])[C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[CH:22]=[CH:21][CH:20]=[C:19]2[S:16]([NH:15][CH2:14][C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[C:7]([OH:33])=[O:6])=[O:32])(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 54264483HCID 54264483, compound

Product 1

HCID 70048380HCID 70048380, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A cold (0° C.), saturated solution of hydrogen chloride in dioxane (400 mL) was added to N-(5-dimethylamino-1-naphthalenesulfonyl)-glycyl-L-proline tert-butyl ester (7.20 g, 15.6 mmol). The mixture was stirred at about 0° C. for about 2 hours and at room temperature for about 2 hours before ether (100 mL) was added. After refrigeration for about 1 hour, the mixture was suction-filtered and afforded 8.30 g (99%) of the title compound as a dense, white solid, m.p. 115°-135° C. (sealed tube); 1H NMR (D2O) δ 8.53 (d, J=8.8 Hz, 1H), 8.30 (d, J=8.7 Hz, 1H), 8.10 (d, J=7.4 Hz, H), 7.95 (d, J=7.8 Hz 1H), 7.74-7.67 (m, 2H), 3.84-3.67 (m, 2H), 3.61 (s, 6H), 3.32-3.17 (m, 2H), 1.96-1.87 (m, 1H), 1.77-1.67 (m, 3H); --C NMR (D2O) ppm 178.17, 178.03, 170.68, 170.34, 141.10, 137.84, 137.61, 133.07, 132.88, 131.39, 130.65, 129.57, 129.24, 128.50, 128.41, 128.11, 122.13, 61.88, 49.52, 49.27, 46.82, 33.44, 31.34, 26.84, 24.32; IR (KBr, cm-1) 3432, 3070, 2960, 1736, 1654, 1440, 1328, 1178, 1146, 1120, 872, 772, 586; MS m/z (MH+ -HCl) calcd 406.1437, obsd 406.1450.

Workup

  1. additionwas added
  2. filtrationthe mixture was suction-filtered

Sources & evidence

ORD record
ord-3a20022334644f3987fe9a061d916820
Source dataset
uspto-grants-1995_01
Patent number
US05380713

Reaction notes

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