N-(tert-butoxycarbonyl)glycine → HCID 135839329, compound

HRID 1861112Notes

Reaction equation

HRID 1861112 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH:6]=[CH:7][C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[CH:22]=[CH:21][C:20]([O:23]COC)=[C:19]([O:27][CH3:28])[CH:18]=4)=[CH:14][CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.C([NH:38][CH2:39][C:40](O)=[O:41])(OC(C)(C)C)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl.CN(C1C=CN=CC=1)C>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([C:13]2[CH:12]=[C:11]3[C:16]([C:8](/[CH:7]=[CH:6]/[C:5]4[CH:29]=[CH:30][C:2]([NH:1][C:40](=[O:41])[CH2:39][NH2:38])=[CH:3][CH:4]=4)=[N:9][NH:10]3)=[CH:15][CH:14]=2)=[CH:18][C:19]=1[O:27][CH3:28]

Participants

6

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69371043HCID 69371043, compound

Product 1

HCID 135839329HCID 135839329, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3-(4-aminostyryl)-6-(3-methoxy-4-methoxymethoxy-phenyl)-1H-indazole (90 mg, 0.224 mmol) was dissolved in dichloromethane (2 mL) and was treated with Boc-glycine (196 mg, 1.12 mmol, 5 equiv), DMAP (82 mg, 3 equiv) and HATU (426 mg, 5 equiv). The mixture was allowed to stir for 30 min. The mixture was partitioned between ethyl acetate and water. The organic material was concentrated, taken up in methanol (5 mL) and was treated with potassium carbonate (100 mg). The mixture was heated to 50° C. for 3 d. The resulting mix was again partitioned between ethyl acetate and water. The organic material was concentrated, and purified by silica (109 mg, 66%): Rf sm 0.32, p 0.46 (ethyl acetate-hexane 6:4); 1H NMR (300 MHz, CDCl3) δ 8.18 (bs, 1H), 8.03 (d, 1H, J=8.1 Hz), 7.56 (m, 5H), 7.40 (m, 3H), 7.20 (m, 3H), 5.29 (s, 2H), 5.20 (bs, 1H), 3.98 (s, 3H), 3.96 (d, 2H), 3.54 (s, 3H), 1.48 (s, 9H).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. concentrationThe organic material was concentrated
  3. additionwas treated with potassium carbonate (100 mg)
  4. additionThe resulting mix
  5. customwas again partitioned between ethyl acetate and water
  6. concentrationThe organic material was concentrated
  7. custompurified by silica (109 mg, 66%)

Sources & evidence

ORD record
ord-2b587f9042b940f295b8be96fe5dedd7
Source dataset
uspto-grants-2003_03
Patent number
US06531491B1

Reaction notes

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