Diisopropylethylamine → (RS)-6-Phenyl-4-(7-phenyl-heptanoylamino)-hexanoic acid

HRID 852894Notes

Reaction equation

HRID 852894 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:5][CH:6]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH2:52][CH:53]([CH2:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[CH2:54][CH2:55][C:56]([OH:58])=[O:57]>CN(C=O)C.CCOCC>[C:61]1([CH2:60][CH2:59][CH:53]([NH:52][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH2:54][CH2:55][C:56]([OH:58])=[O:57])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5209877-Phenyl heptanoic acidHCID 11171785(RS)-4-Amino-6-phenyl-hexanoic acid

Product 1

HCID 23644455(RS)-6-Phenyl-4-(7-phenyl-heptanoylamino)-hexanoic acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Phenylheptanoic acid (105 mg 0.51 mmol) and BOP (250 mg, 0.56 mmol) were dissolved in dry DMF 2 mL then DIPEA 200 μL was added. After mixing for 3 min the solution was added to (RS)-4-amino-6-phenyl-hexanoic acid (101) (105 mg, 0.51 mmol) and the solution was stirred at room temperature for 1 hr. Ether was added and the solution was washed twice with 1 M HCl and brine then dried over MgSO4. Removal of solvent gave a white solid 200 mg, which was recrystallised from EtOAc-hexane. 1H NMR (300 MHz, CDCl3) δ 7.30-7.22 (m, 4H), 7.21-7.11 (m, 6H), 6.17 (br, 1H, NH), 4.02 (m, 1H), 2.70-2.53 (m, 4H), 2.38 (m, 2H), 2.22 (m, 2H), 2.00-1.52 (m, 8H), 1.44-1.27 (m, 4H).

Workup

  1. additionAfter mixing for 3 min the solution
  2. washthe solution was washed twice with 1 M HCl and brine
  3. dry with materialthen dried over MgSO4
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-8777bb1f211540d0ac201bd12066880a
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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