1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178424990, compound

HRID 2414394Notes

Reaction equation

HRID 2414394 reaction equation
C(CC[N:5]1[C:9]([C:10]2[CH:11]=[C:12]([CH:38]=[CH:39][CH:40]=2)[CH2:13][O:14][CH2:15][C@@H:16]([NH:19][C:20](=[O:37])[C@H:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[CH:31]=2)[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]#[N:18])=[N:8][N:7]=[N:6]1)#N.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[NH:8]1[C:9]([C:10]2[CH:11]=[C:12]([CH:38]=[CH:39][CH:40]=2)[CH2:13][O:14][CH2:15][C@@H:16]([NH:19][C:20](=[O:37])[C@H:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[CH:31]=2)[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]#[N:18])=[N:5][N:6]=[N:7]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23533835HCID 23533835, compound

Product 1

HCID 178424990HCID 178424990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-[3-(1-(2-cyanoethyl)-5-tetrazolyl)-benzyloxy]-1(S)-cyanoethyl]-3-methyl-Nα-phenyl-L-phenylalaninamide (prepared according to examples 1(g) and 7 using intermediate of Example 1(e)), 160 mg, 0.30 mmol) in CH2Cl2 (10 mL) is added DBU (0.22 mL, 1.5 mmol) in one portion, and the solution is stirred at room temp. for 2 h., after which time the solution is washed with 1 N HCl (30 mL), brine (30 mL), dried (MgSO4), evaporated, and chromatographed (2% MeOH/CH2Cl2, 0 to 0.05% acetic acid) to yield N-[2-[3-(5-tetrazolyl)-benzyloxy]-1(S)-cyanoethyl]-3-methyl-Nα-phenyl-phenylalaninamide, as an off-white solid; m.p. 120-122° C.

Workup

  1. washafter which time the solution is washed with 1 N HCl (30 mL), brine (30 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customchromatographed (2% MeOH/CH2Cl2, 0 to 0.05% acetic acid)

Sources & evidence

ORD record
ord-17c44559cbbd40db8931de647f56d417
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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