Diisopropylethylamine → HCID 19422641, compound

HRID 744909Notes

Reaction equation

HRID 744909 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:18]([OH:20])=O)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:25][CH:24]=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)C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C.O>[C:38]([O:37][C:35]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:26]1[CH:25]=[CH:24][C:23]([CH2:22][NH:21][C:18]([C:12]2([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[O:20])=[CH:28][CH:27]=1)=[O:36])([CH3:41])([CH3:39])[CH3:40]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 99710734'-(Aminomethyl)-biphenyl-2-carboxylic acid 1,1-dimethylethyl esterHCID 194226274-{[(Benzyloxy)carbonyl]amino}oxane-4-carboxylic acid

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-e0b2b56613fe4b299bdf2c390d534a16
Source dataset
uspto-grants-1996_09
Patent number
US05559233

Reaction notes

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