Triethylamine → HCID 89689438, compound

HRID 710256Notes

Reaction equation

HRID 710256 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)[CH2:3][OH:4].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][O:22][C@@H:21]([C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=2)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C@@H:2]([NH:1][C:29]([C:28]2[CH:27]=[CH:26][C:25]([C@@H:21]3[O:22][CH2:23][CH2:24][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:20]3)=[CH:33][CH:32]=2)=[O:30])[CH2:3][OH:4])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10583003(R)-2-Amino-2-(4-fluorophenyl)ethanolHCID 668420684-(1,1-Dimethylethyl) (2S)-2-(4-carboxyphenyl)-4-morpholinecarboxylate

Product 1

HCID 89689438HCID 89689438, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-2-amino-2-(4-fluorophenyl)ethanol (68.6 mg, 0.44 mmol), (S)-4-(4-(tert-butoxycarbonyl)morpholin-2-yl)benzoic acid [CAS 1131220-40-0], (136 mg, 0.44 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (170 mg, 0.88 mmol), 4-dimethylaminopyridine (54.0 mg, 0.44 mmol) and triethylamine (179 mg, 0.25 ml, 1.77 mmol) in dichloromethane (9 ml) was stirred at room temperature overnight. The reaction was quenched by addition of 1M citric acid solution (5 ml). The organic layer was separated, washed with sodium bicarbonate saturated solution (5 ml), dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (silica gel, gradient heptane/ethyl acetate), to give a white foam (100 mg, 51%), MS (ISP): 445.4 (100%, [M-tBu+H]+), 389.3 (29%, [M+H]+).

Workup

  1. customThe reaction was quenched by addition of 1M citric acid solution (5 ml)
  2. customThe organic layer was separated
  3. washwashed with sodium bicarbonate saturated solution (5 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude material was purified by flash chromatography (silica gel, gradient heptane/ethyl acetate)

Sources & evidence

ORD record
ord-990fb4092e274f39a6c3fa5c5c5c070b
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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