Diisopropylethylamine → HCID 57695553, compound

HRID 2079861Notes

Reaction equation

HRID 2079861 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]2[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=2[O:32][CH3:33])=[CH:11][C:10]=1[C:34](O)=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:70][CH:71]1[CH2:76][CH2:75][N:74]([C:77]([O:79][C:80]([CH3:83])([CH3:82])[CH3:81])=[O:78])[CH2:73][CH2:72]1>CN(C=O)C.C(OCC)(=O)C>[C:80]([O:79][C:77]([N:74]1[CH2:73][CH2:72][CH:71]([NH:70][C:34]([C:10]2[CH:11]=[C:12]([C:23]3[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=3[O:32][CH3:33])[C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:35])[CH2:76][CH2:75]1)=[O:78])([CH3:83])([CH3:82])[CH3:81]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57695593HCID 57695593, compound

Product 1

HCID 57695553HCID 57695553, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid (4.4 g, 9.2 mmol), diisopropylethylamine (3.2 ml, 18.3 mmol) and HBTU (5.2 g, 13.7 mmol) in anhydrous DMF (44 ml) was charged 4-amino-1-N-Boc-piperidine (2.3 g, 11.4 mmol). The mixture was stirred at rt for 16 h. The reaction mixture was then diluted with ethyl acetate and washed with water. The organics were then dried (Na2SO4), filtered and evaporated to yield 4-[(4,6-bis-benzyloxy-5′isopropyl-2′methoxy-biphenyl-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a brown solid (6.1 g, quant.), carried forward without further purification. M.p.: 168-170° C.; 400 MHz 1H NMR (CDCl3) δ: 8.16 (s, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.42 (s, 4H), 7.34-7.26 (m, 6H), 7.18 (dd, J=8.4, 2.0 Hz, 1H), 7.14 (s, 1H), 6.87 (d, J=8.4 Hz, 1H), 6.64 (s, 1H), 5.12 (s, 2H), 5.05 (s, 2H), 4.07 (m, 1H), 3.73 (s, 3H), 3.56 (br s, 2H), 2.90 (m, 2H), 1.78 (d, J=7.2 Hz, 2H), 1.57 (s, 1H), 1.47 (s, 9H), 1.24 (d, J=7.2 Hz, 6H), 1.08 (m, 2H); LCMS: 576 [M+H].

Workup

  1. washwashed with water
  2. dry with materialThe organics were then dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-1c7f8db30e7c404f8ce1c543777fa230
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

Loading…