Diisopropylethylamine → HCID 19422641, compound

HRID 1707412Notes

Reaction equation

HRID 1707412 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22]([C:24]2([NH:29][C:30]([O:32][CH2:33]C3C4C(=CC=CC=4)C4C3=CC=CC=4)=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NCC1C=CC(C2C=CC=CC=2C(OC(C)(C)C)=[O:62])=CC=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:88]2[CH:89]=[CH:90][CH:91]=[CH:92][C:87]=2N=N1>CN(C=O)C.C(OCC)(=O)C.O>[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][NH:21][C:22]([C:24]2([NH:29][C:30]([O:32][CH2:33][C:87]3[CH:88]=[CH:89][CH:90]=[CH:91][CH:92]=3)=[O:31])[CH2:25][CH2:26][O:62][CH2:27][CH2:28]2)=[O:23])=[CH:18][CH:19]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 99710734'-(Aminomethyl)-biphenyl-2-carboxylic acid 1,1-dimethylethyl esterHCID 19422617N-(2'-Tert-butoxycarbonylbiphenyl-4-ylmethyl)-1-(N-Fmoc-amino)cyclopentane-1-carboxamide

Product 1

HCID 19422641HCID 19422641, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

850 mg of the compound prepared in step B are dissolved in 15 ml of DMF, and equimolar amounts of 4-aminomethyl-2'-tert-butoxycarbonylbiphenyl, DIPEA and then BOP (10% excess) are added. After 40 minutes, the medium is taken up in 200 ml of ethyl acetate and 200 ml of water. The organic phase is decanted and then washed twice with a saturated solution of sodium bicarbonate, twice with a 5% solution of sodium bisulfate and then once with a saturated solution of sodium chloride. After drying over sodium sulfate, the organic phase is evaporated under vacuum to give 1.8 g of the expected product.

Workup

  1. customThe organic phase is decanted
  2. washwashed twice with a saturated solution of sodium bicarbonate, twice with a 5% solution of sodium bisulfate
  3. dry with materialAfter drying over sodium sulfate
  4. customthe organic phase is evaporated under vacuum

Sources & evidence

ORD record
ord-50cf3292660b4c85a5fa4691eb987fee
Source dataset
uspto-grants-1994_10
Patent number
US05352788

Reaction notes

Loading…