Sodium Bicarbonate → HCID 86678375, compound

HRID 882625Notes

Reaction equation

HRID 882625 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:62])[C@H:6]([C:10]([NH:12][C@H:13]([C:17]([N:19]([C@@H:21]([C@@H:58]([CH3:61])[CH2:59][CH3:60])[C@H:22]([O:56][CH3:57])[CH2:23][C:24]([N:26]1[CH2:30][CH2:29][CH2:28][C@H:27]1[C@H:31]([O:54][CH3:55])[C@@H:32]([CH3:53])[C:33]([NH:35][C@@:36]1([C:45]([N:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)=[O:46])[CH2:38][C@@H:37]1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:34])=[O:25])[CH3:20])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH:7]([CH3:9])[CH3:8].C(=O)([O-])O.[Na+].[O:68]=[C:69]1[CH:73]=[CH:72][C:71](=[O:74])N1C(OC)=O>O1CCOCC1>[O:68]=[C:69]1[CH:73]=[CH:72][C:71](=[O:74])[N:1]1[CH2:2][CH2:3][CH2:4][N:5]([CH3:62])[C@H:6]([C:10]([NH:12][C@H:13]([C:17]([N:19]([C@@H:21]([C@@H:58]([CH3:61])[CH2:59][CH3:60])[C@H:22]([O:56][CH3:57])[CH2:23][C:24]([N:26]1[CH2:30][CH2:29][CH2:28][C@H:27]1[C@H:31]([O:54][CH3:55])[C@@H:32]([CH3:53])[C:33]([NH:35][C@@:36]1([C:45]([N:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)=[O:46])[CH2:38][C@@H:37]1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:34])=[O:25])[CH3:20])=[O:18])[CH:14]([CH3:15])[CH3:16])=[O:11])[CH:7]([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 580610N-(Methoxycarbonyl)maleimideHCID 86678376HCID 86678376, compound2×

Product 1

HCID 86678375HCID 86678375, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12 mg (14 μmol) of N-(3-aminopropyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino}-3-oxopropyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide (Intermediate 66) were taken up in 750 μl of dioxane and admixed with 1.5 ml of saturated sodium hydrogencarbonate solution and then with 3.2 mg (21 μmol) of methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate. The reaction mixture was stirred at RT for 1 h and then concentrated under reduced pressure. The remaining residue was purified by means of preparative HPLC. After lyophilization, 4.2 mg (32% of theory) of the title compound were obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe remaining residue was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-fb3af223020a479f93fb87873ee89a63
Source dataset
uspto-grants-2015_03
Patent number
US08992932B2

Reaction notes

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