1-Hydroxy-2-naphthoic acid → HCID 58865420, compound

HRID 1354827Notes

Reaction equation

HRID 1354827 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:48]([O:52][C:53]([NH:55][C@@H:56]1[CH2:61][C@H:60]([NH:62][C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:59][N:58]([C:70]2[CH:75]=[C:74]([NH:76][C:77]3[CH:82]=[CH:81][C:80]([NH2:83])=[CH:79][CH:78]=3)[CH:73]=[C:72]([N:84]3[CH2:89][C@@H:88]([NH:90][C:91]([O:93][C:94]([CH3:97])([CH3:96])[CH3:95])=[O:92])[CH2:87][C@@H:86]([NH:98][C:99]([O:101][C:102]([CH3:105])([CH3:104])[CH3:103])=[O:100])[CH2:85]3)[N:71]=2)[CH2:57]1)=[O:54])([CH3:51])([CH3:50])[CH3:49]>CN(C=O)C.CCOC(C)=O>[C:48]([O:52][C:53]([NH:55][C@@H:56]1[CH2:61][C@H:60]([NH:62][C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:59][N:58]([C:70]2[CH:75]=[C:74]([NH:76][C:77]3[CH:82]=[CH:81][C:80]([NH:83][C:12]([C:3]4[CH:4]=[CH:5][C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C:2]=4[OH:1])=[O:14])=[CH:79][CH:78]=3)[CH:73]=[C:72]([N:84]3[CH2:89][C@@H:88]([NH:90][C:91]([O:93][C:94]([CH3:97])([CH3:96])[CH3:95])=[O:92])[CH2:87][C@@H:86]([NH:98][C:99]([O:101][C:102]([CH3:105])([CH3:104])[CH3:103])=[O:100])[CH2:85]3)[N:71]=2)[CH2:57]1)=[O:54])([CH3:49])([CH3:50])[CH3:51]

Participants

7

Reactant 4

HCID 68441-Hydroxy-2-naphthoic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58865722HCID 58865722, compound

Product 1

HCID 58865420HCID 58865420, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Hydroxy-naphthalene-2-carboxylic acid (142) (0.028 g, 0.148 mmol) was dissolved in DMF (1 mL), iPr2EtN (0.222 mmol) was added followed by 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl-uronium hexafluorophosphate (HBTU) (0.062 g, 0.163 mmol) and the mixture was shaken in an 8 mL Teflon septum capped vial at room temperature for 20 minutes. N-(2,6-bis-((3R,5S)-3,5-bis-(tert-butoxycarbonylamino)-piperidin-1-yl)-pyridin-4-yl)-benzene-1,4-diamine (141) (0.08 g, 0.0986 mmol) was added and the mixture was shaken at room temperature for 16 h. LC-MS indicated complete coupling at this point. The mixture was diluted with EtOAc (25 mL), washed with water (15 mL), NaHCO3 (aqueous sat., 15 mL) and brine (15 mL) via extraction, dried over MgSO4 and concentrated to give an orange/green oil. Purification by flash chromatography using a gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane in 30 minutes) gave the desired product (143) as a greenish-white powder upon concentration (0.063 g, 0.064 mmol, 65% yield). LC-MS (ESI): (exact mass: 981.53) m/e=982.6 [M+1]+ (100%).

Workup

  1. customcapped vial at room temperature for 20 minutes
  2. washwashed with water (15 mL), NaHCO3 (aqueous sat., 15 mL) and brine (15 mL) via extraction
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give an orange/green oil
  6. customPurification by flash chromatography
  7. customa gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane in 30 minutes)

Sources & evidence

ORD record
ord-e923430f728540fd9147da1a053a5353
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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