Heptanoic Acid → HCID 54165626, compound

HRID 1989847Notes

Reaction equation

HRID 1989847 reaction equation
[C:1]([OH:9])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[NH2:10][C@H:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:12][OH:13].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CCCCCC.CCOC(C)=O>[CH3:17][O:16][C:14](=[O:15])[C@H:11]([CH2:12][OH:13])[NH:10][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

8

Reactant 5

HCID 8094Heptanoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723731(S)-methyl 2-amino-3-hydroxypropanoateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 54165626HCID 54165626, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of heptanoic acid (0.46 ml, 3.2 mmol) and H-Ser-OCH3 (0.5 g, 3.2 mmol) in CH2Cl2 (15 ml) were added HBTU (1.83 g, 4.8 mmol), HOBt (0.74 g, 4.8 mmol) and lastly diisopropylethylamine (2.8 ml, 16 mmol). Reaction was stirred overnight at room temperature. The resulting mixture was subjected to flash column chromatography (hexane/EtOAc, 1:2) yielding (S)—N-heptanoyl-serine methyl ester (588.6 mg, 79%) as yellowish oil. 1H NMR: δ=6.47 (b, 1H, NH), 4.69 (m, 1H, 2-H), 3.94 (m, 2H, 3-H), 3.79 (s, 3H, 1-OCH3), 2.27 (t, 3J=7.6 Hz, 2H, 2′-H), 1.63 (m, 2H, HHep), 1.29 (m, 6H, HHep), 0.88 (m, 3H, 7′-CH3) ppm.

Workup

  1. customReaction

Sources & evidence

ORD record
ord-d16d7970c13a4ded89ba5cfe90927ede
Source dataset
uspto-grants-2010_01
Patent number
US07642369B2

Reaction notes

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