Lithium Hydroxide → HCID 71817940, compound

HRID 1478650Notes

Reaction equation

HRID 1478650 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:42])[NH:10][C@@H:11]([CH2:36][C:37]2[N:38]=[CH:39][S:40][CH:41]=2)[C:12](=[O:35])[NH:13][CH2:14][C:15]2[N:16]=[N:17][N:18]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH:19]=2)[O:7]1)=[O:5])C.[Li+].[OH-]>>[O:35]=[C:12]([NH:13][CH2:14][C:15]1[N:16]=[N:17][N:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)[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:42])[CH2:36][C:37]1[N:38]=[CH:39][S:40][CH:41]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 131736520HCID 131736520, compound

Product 1

HCID 71817940HCID 71817940, compoundYield 48.3%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 40 (26 mg, 0.42 mmol); LiOH (1.0 mg, 0.04 mmol); after extraction afforded the desired product as a white solid (12 mg, 48.3%). 1H NMR (Acetone-d6, 400 MHz): δ8.98 (bs, 1H); 8.48 (s, 1H); 8.16-8.12 (d, 2H, 8.48); 8.02-8.00 (d, 2H, J=8.48 Hz); 7.37 (bs, 1H); 4.81 (bs, 1H); 4.52 (s, 2H); 3.85-3.79 (m, 4H); 3.61 (s, 1H); 3.55 (s, 1H); 1.82-1.60 (m, 6H). 13C NMR (Acetone-d6, 100 MHz): 170.07, 169.01, 165.12, 153.52, 139.36, 136.19, 129.47, 120.84, 120.21, 107.39, 107.25, 66.62, 53.44, 52.80, 52.77, 46.83, 32.52, 30.07, 25.02, 23.13. HRMS-ESI: m/z [M+H+] calculated for C24H27N7O7S2: 590.6440, observed: m/z 590.1050 (M+H+); HPLC Method 2: Rt=21.7 min; purity=96.3%.

Workup

  1. extractionafter extraction

Sources & evidence

ORD record
ord-30c41bcb175c45bd87e25af8225b5e22
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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