Triphenylphosphine → HCID 59370744, compound

HRID 1873979Notes

Reaction equation

HRID 1873979 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:8]([O:21][Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:9][N:10]([CH2:18][CH2:19][OH:20])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1.O[C:30]1[CH:38]=[C:37]2[C:33]([C:34]([CH:46]3[CH2:48][CH2:47]3)=[N:35][N:36]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C(=O)([O-])[O-]>C1(C)C=CC=CC=1.C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:8]([O:21][Si:22]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:27][CH3:28])[CH2:9][N:10]([C:11]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:17])[CH2:18][CH2:19][O:20][C:30]2[CH:38]=[C:37]3[C:33]([C:34]([CH:46]4[CH2:48][CH2:47]4)=[N:35][N:36]3[C:39]([O:41][C:42]([CH3:44])([CH3:45])[CH3:43])=[O:40])=[CH:32][CH:31]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 19660Carbonate IonHCID 5363146Diisopropyl azodicarboxylateHCID 59370757HCID 59370757, compoundHCID 135869950HCID 135869950, compound

Product 1

HCID 59370744HCID 59370744, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

(R)-Tert-butyl 2-(3-aminophenyl)-2-(triethylsilyloxy)ethyl(2-hydroxyethyl)carbamate (1.6143 g) which can be prepared according to the method described in Reference example 59, etc. and tert-butyl 6-hydroxy-3-cyclopropylindazole-1-carboxylate (924 mg) which can be prepared according to the method described in Reference example 7, etc. and triphenylphosphine (1.1419 g; manufactured by Kanto Chemical Co., Inc.) were dissolved in dehydrated toluene (18 mL), added with DIAD (808 μL; manufactured by Sigma-Aldrich Co.), and stirred overnight at room temperature. The reaction solution was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=82:18→61:39) to obtain a crude product (1.669 g), which was then dissolved in CH2Cl2 (20 mL). After adding MP-Carbonate [5.15 g (2.73 mol/g); manufactured by Argonaut] to the mixture, it was stirred overnight at room temperature. After filtering the reaction solution, the filtrate was concentrated under reduced pressure to obtain the title compound (1.0644 g).

Workup

  1. customcan be prepared
  2. customThe reaction solution was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=82:18→61:39)
  3. customto obtain a crude product (1.669 g), which
  4. stirringwas stirred overnight at room temperature
  5. filtrationAfter filtering the reaction solution
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a77ae661824d48838369dd7ca0a3e8da
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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