4-Methylmorpholine → HCID 10636385, compound

HRID 1593305Notes

Reaction equation

HRID 1593305 reaction equation
[NH2:1][C@@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].Cl.[OH:14][C@@H:15]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:16](O)=[O:17].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>ClCCl>[OH:14][C@@H:15]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:16]([NH:1][C@@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4])=[O:17]

Participants

7

Reactant 5

HCID 79724-Methylmorpholine2×HCID 757711-HydroxybenzotriazoleHCID 1201451Methyl phenylglycinate, L-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86604641HCID 86604641, compound

Product 1

HCID 10636385HCID 10636385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of methyl (2S)-amino(phenyl)acetate (3.06 g), (2S)-2-hydroxy-4-methylpentanoic acid hydrochloride, NMM (1.85 ml), and HOBt (6.15 g) in dichloromethane (50 ml) was added EDAC-HCl (5.81 g). Additional NMM (2.31 ml) was then added. The mixture was stirred for 2h at 0° C., then overnight at RT. The reaction was concentrated and the residue was taken up in Ethyl acetate washed with 0.1N hydrochloric acid, saturated sodium bicarbonate, brine, dried, filtered and evaporated to afford the title compound (4.20 g). 1H NMR (300 MHz, CDCl3) δ 0.92-0.95 (m, 6H), 1.47-1.67 (m, 2H), 1.76-2.04 (m, 1H), 2.63 (bs, 1H), 3.74 (s, 3H), 4.21 (d, 1H, J=9 Hz), 5.58 (d, 1H, J=8 Hz), 7.26-7.42 (m, 5H). MS APCI, m/z=280 (M+1). LC/MS: 1.95 min.

Workup

  1. customovernight
  2. customat RT
  3. concentrationThe reaction was concentrated
  4. washwashed with 0.1N hydrochloric acid, saturated sodium bicarbonate, brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3e251dffe6cb43b6a6f3f00c516c0a38
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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