Triethylamine → HCID 15453141, compound

HRID 1067091Notes

Reaction equation

HRID 1067091 reaction equation
[C:1]([NH:8][C@H:9]([CH2:24][OH:25])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(N(CC)CC)C>ClCCl>[CH3:26][S:27]([O:25][CH2:24][C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11772551Nalpha-Boc-Ndelta-Cbz-ornithinol

Product 1

HCID 15453141HCID 15453141, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Nα-Boc-Nδ-Cbz-ornithinol (363 mg) in dichloromethane (10 ml) at 0° C., under nitrogen atmosphere, was treated sequentially with methanesulfonyl chloride (110 μl, 1.4 eq) and triethylamine (200 μl, 1.4 eq). After 3 hrs, the solution was poured into dichloromethane and worked up as usual. The crude product, which is very pure (400 mg), is a white solid: 1H NMR (400 MHz, CDCl3) δ1.45 (s, 9H), 1.63 (m, 4H), 3.02 (s, 3H), 3.24 (m, 2H), 3.84 (m, 1H), 4.19 (dd, J=9.5; 3.7 Hz, 1H), 4.23 (d, J=9.5 Hz, 1H), 5.14 (s, 2H), and 7.39 (m, 5H).

Sources & evidence

ORD record
ord-559d9c18a6394a78a97a53cd2003513c
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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