Diisopropylethylamine → HCID 58746941, compound

HRID 724740Notes

Reaction equation

HRID 724740 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[C:16]([Cl:21])[CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[NH2:50][CH2:51][C:52]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:53].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[Cl:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[I:20])[CH2:13][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10](=[O:12])[NH:50][CH2:51][C:52](=[O:53])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 69597869HCID 69597869, compound

Product 1

HCID 58746941HCID 58746941, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(3-chloro-4-iodophenyl)propanoic acid (4.16 g, 9.77 mmol) in DMF (80 mL) was treated with benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (4.6 g, 10.0 mmol). After 10 minutes at rt the solution was treated with a solution of 2-amino-1-phenylethanone hydrochloride (2.52 g, 14.6 mmol) and N,N-diisopropylethylamine (8.5 mL, 49.0 mmol). The solution was stirred at rt for 2 h. The solution was diluted with ethyl acetate (250 mL) and washed with saturated aqueous sodium bicarbonate solution (200 mL). The organic phase was dried over sodium sulfate. Purification by silica gel chromatography (5–25% ethyl acetate:hexanes) afforded product as a white solid (3.1 g, 58%). LCMS found for C22H25ClIN2NaO4 (M+Na)+: m/z=565.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (200 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customPurification by silica gel chromatography (5–25% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-f0bf45fd9b964776ad0fd580e447c61e
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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