Water → Dicyclohexylcarbodiimide

HRID 742436Notes

Reaction equation

HRID 742436 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)C=C[C:2]=1C(C)C(O)=S.[CH:16]1[CH:17]=[CH:18][C:19]2N(O)N=[N:22][C:20]=2[CH:21]=1.O.O1CCCC1>CN(C)C=O>[CH2:17]1[CH2:16][CH2:21][CH:20]([N:22]=[C:2]=[N:1][CH:10]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 178460588HCID 178460588, compound

Product 1

HCID 10868Dicyclohexylcarbodiimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The subtitled compound was prepared substantially in accordance with the procedure detailed in Example 1A using 1.8 g (5.2 mmol) of the subtitled compound of Preparation 1D, 1.8 g (5.2 mmol) of (2S)-2-N(t-butoxycarbonyl)amino-4-(quinolin-2-ylthiopropanoic acid, 0.70 g (5.2 mmol) of HOBT.H2O and 1.1 g (5.2 mmol) of DCC, in a 15 mL of tetrahydrofuran containing 2 mL of dimethylformamide, to provide 3.1 g of a yellow solid. This solid was purified using flash chromatography (eluent of 35% ethyl acetate in toluene) to provide 1.8 g of a white solid. Yield: 51%. 1H NMR (CDCl3): δ1.40 (s, 9 H), 1.45 (s, 9 H), 2.95 (m, 4 H) , 3.57 (d, J=4 Hz, 2 H), 3.65 (m, 1 H), 4.30 (m, 1 H), 4.52 (q, J=5 Hz, 1 H), 6.02 (br.s, 2 H), 6.85 (d, J=9 Hz, 1 H), 7.10-7.38 (m, 10 H), 7.46 (t, J=7 Hz, 1 H), 7.70 (m, 2 H), 7.90 (d, J=9 Hz, 1 H), 8.04 (d, J=8 Hz, 1 H). MS (FD): m/e 670 (M+). IR (KBr): 3292, 1715, 1637, 1594, 1518 cm-1. UV (EtOH): 210 nm (E=58,247), 257 nm (E=23,586), 327 nm (E=5,628), 339 nm (E=6,082).

Workup

  1. customThe subtitled compound was prepared substantially in accordance with the procedure

Sources & evidence

ORD record
ord-bdb3e046b554450bb1365ae3b222cc8b
Source dataset
uspto-grants-1996_09
Patent number
US05554653

Reaction notes

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