Sodium Hydroxide → HCID 22887906, compound

HRID 992248Notes

Reaction equation

[OH-].[Na+].[CH3:3][O:4][C:5]1[N:9]=[C:8]([NH:10][C:11]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12])[S:7][N:6]=1.Cl.[NH:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=[O:26]>>[CH3:3][O:4][C:5]1[N:9]=[C:8]([NH:10][C:11]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:12])[S:7][N:6]=1.[NH:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=[O:26]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 86756121HCID 86756121, compound

Product 1

HCID 22887906HCID 22887906, compound

Procedure

In a similar manner as shown in example 18, base saponification of 3-methoxy-5-(N-L-leucine-L-proline)carbamoyl-[1,2,4]-thiadiazole methyl ester using a solution of 1N sodium hydroxide followed by acidification using a solution of 1N HCl {3-methoxy-[1,2,4]-thiadiazol-5-yl}carbamoyl-L-leucine-L-proline as a white solid (55%). M.p. 209-211° C.; 1H-NMR (MeOD) δ 4.64-4.67 (dd, J=8.1, 2.3 Hz, 1H, NCH), 4.44-4.45 (m, 1H, NCHpro), 3.94 (s, 3H, OMe), 3.60-3.86 (m, 2H, NCH2pro), 1.54-2.27 (m, 6H, 3CH2), 0.94-1.01 (two d, J=6.4 Hz, 7H, 2CH3+CH); MS (m/z) 386 (M++1), 271, 229, 158, 116, 86.

Sources & evidence

ORD record: ord-27723e71b76a4740a93edb9b4f54e450
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468977B1

Reaction notes

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