Sodium Bicarbonate → HCID 69675376, compound

HRID 1751715Notes

Reaction equation

HRID 1751715 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:6]([C:16]2[NH:17][C:18]([C:21]3[CH:22]=[C:23]4[CH2:36][O:35][C:34]5[C:25]6=[C:26]([CH:31]=[C:32]([C:37]7[NH:41][C:40]([C@@H:42]8[CH2:46][C@H:45]([CH3:47])[CH2:44][NH:43]8)=[N:39][CH:38]=7)[CH:33]=5)[CH2:27][O:28][C:29]([CH:30]=3)=[C:24]46)=[CH:19][N:20]=2)[CH2:5]1.[CH3:48][O:49][C:50]([NH:52][C@H:53]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:54](O)=[O:55])=[O:51].CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+]>CCN(C(C)C)C(C)C.CN(C=O)C>[CH3:48][O:49][C:50]([NH:52][C@H:53]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:54]([N:43]1[CH2:44][C@@H:45]([CH3:47])[CH2:46][C@H:42]1[C:40]1[NH:41][C:37]([C:32]2[CH:33]=[C:34]3[O:35][CH2:36][C:23]4[C:24]5[C:25]3=[C:26]([CH2:27][O:28][C:29]=5[CH:30]=[C:21]([C:18]3[NH:17][C:16]([C@@H:6]5[CH2:5][C@H:4]([CH2:3][O:2][CH3:1])[CH2:8][N:7]5[C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])=[N:20][CH:19]=3)[CH:22]=4)[CH:31]=2)=[CH:38][N:39]=1)=[O:55])=[O:51]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 86708809HCID 86708809, compound

Product 1

HCID 69675376HCID 69675376, compoundYield 185.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A mixture of (2S,4S)-tert-butyl 4-(methoxymethyl)-2-(5-(7-(2-((2S,4S)-4-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)-5,10-dihydrochromeno[5,4,3-cde]chromen-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (102 mg, 0.159 mmol), (R)-2-(methoxycarbonylamino)-2-phenylacetic acid (33 mg, 0.159 mmol), COMU (75 mg, 0.175 mmol) in 1.59 mL 10% DIPEA in DMF was stirred at room temperature for 1 hr. Saturated sodium bicarbonate was added and the crude product was extracted into ethyl acetate. Concentration and purification by silica gel chromatography gave product (245 mg).

Workup

  1. extractionthe crude product was extracted into ethyl acetate
  2. concentrationConcentration and purification by silica gel chromatography

Sources & evidence

ORD record
ord-1d8280d62135443399981216c56b97b9
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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