Triethylamine → HCID 67634307, compound

HRID 2293359Notes

Reaction equation

HRID 2293359 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH2:9]([NH:16][C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.Br[CH2:33][C:34]([C:36]12[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][CH:38]([CH2:39]3)[CH2:37]1)[CH2:43]2)=[O:35]>C1COCC1>[C:36]12([C:34](=[O:35])[CH2:33][N:1]3[CH2:8][CH2:7][CH2:6][C@H:2]3[C:3]([N:16]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5])[CH2:43][CH:42]3[CH2:41][CH:40]([CH2:39][CH:38]([CH2:44]3)[CH2:37]1)[CH2:45]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketoneHCID 86751513HCID 86751513, compound

Product 1

HCID 67634307HCID 67634307, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, treatment of a solution of L-proline-L-isoleucine benzylamide (160.7 mg, 0.50 mmol), with triethylamine (3.53 mL, 2.53 mmol, 5.0 eq), and 1-adamantyl bromomethyl ketone (156 mg, 0.61 mmol, 1.2 eq) in THF (20 mL), provided 180 mg (99%) of L-isoleucine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-Prolyl] benzylamide as a white foam.

Sources & evidence

ORD record
ord-57ad4e0bfdbb4ac0a20615078cf857a4
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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