Sodium Ascorbate → HCID 178511006, compound

HRID 2206345Notes

Reaction equation

HRID 2206345 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C:42]([OH:44])=[O:43])[NH:9][C:10](=[O:41])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:40])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([C:37]([OH:39])=[O:38])[NH:24][C:25](=[O:36])[NH:26][C@H:27]([C:33]([OH:35])=[O:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[N+:2]=[N-:3].[NH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH:50]([NH:54][C:55](=[O:71])[CH:56]([NH:66][C:67](=[O:70])[C:68]#[CH:69])[CH2:57][CH2:58][CH2:59][CH2:60][NH:61][C:62](=[O:65])[C:63]#[CH:64])[C:51]([OH:53])=[O:52].[O:72]=[C:73]1[O:79][C@H:78]([C@H:80]([CH2:82]O)O)[C:76]([O-])=[C:74]1O.[Na+]>O.CC(O)(C)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH:50]([NH:54][C:55](=[O:71])[CH:56]([NH:66][C:67]([C:68]1[N:1]=[N:2][NH:3][C:69]=1[CH2:82][CH2:80][CH2:78][CH2:76][CH:74]([C:73]([OH:79])=[O:72])[NH:9][C:10](=[O:41])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:40])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([C:37]([OH:39])=[O:38])[NH:24][C:25](=[O:36])[NH:26][CH:27]([C:33]([OH:35])=[O:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:70])[CH2:57][CH2:58][CH2:59][CH2:60][NH:61][C:62]([C:63]1[N:3]=[N:2][N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C:42]([OH:44])=[O:43])[NH:9][C:10](=[O:41])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:40])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([C:37]([OH:39])=[O:38])[NH:24][C:25](=[O:36])[NH:26][CH:27]([C:33]([OH:35])=[O:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:64]=1)=[O:65])[C:51]([OH:53])=[O:52]

Participants

6

Reactant 3

HCID 23667548Sodium AscorbateHCID 89600888HCID 89600888, compoundHCID 117700439HCID 117700439, compound

Product 1

HCID 178511006HCID 178511006, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

Compound 1 (49 mg, 76.7 μM) and 4 (0.5 eq, 14.5 mg, 38.3 μM) were dissolved in 1 mL H2O/t-BuOH (1/1). To that solution, sodium ascorbate (6 mg, 30 μM) and Cu(OAc)2 (3 mg, 15 μM) were added consecutively, the mixture was purged with N2 gas and stirred at ambient temperature overnight. Compound 2 was purified using C18 SepPak® Vac 2 g column through which the product was successfully eluted using 70/30 water/acetonitrile (0.1% TFA). Compound 2 was further purified by HPLC (Method 1). Rt: 13.9 min. ESI-MS m/Z: 1638 [M+H]+.

Workup

  1. customthe mixture was purged with N2 gas
  2. customCompound 2 was purified
  3. washwas successfully eluted
  4. customCompound 2 was further purified by HPLC (Method 1)

Sources & evidence

ORD record
ord-2777fbe4486642b7ba1004b52714def4
Source dataset
uspto-grants-2016_06
Patent number
US09371360B2

Reaction notes

Loading…