4-Methylmorpholine → HCID 59479671, compound

HRID 76321Notes

Reaction equation

HRID 76321 reaction equation
[N:1]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([NH:5][CH2:6][C:7]([OH:9])=O)=[O:4].CN1CCOCC1.[NH2:27][CH2:28][CH2:29][CH2:30][OH:31]>C1COCC1.CCOC(C)=O>[N:1]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([NH:5][CH2:6][C:7]([NH:27][CH2:28][CH2:29][CH2:30][OH:31])=[O:9])=[O:4]

Participants

6

Reactant 3

HCID 79724-Methylmorpholine2×HCID 90863-Amino-1-propanolHCID 70198962-(((2S)-1-((tert-butoxy)carbonyl)pyrrolidin-2-yl)formamido)acetic acid

Product 1

HCID 59479671HCID 59479671, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a cold (−15° C.) solution of Boc-Pro-Gly-OH (610 mg, 2.24 mmol) and NMM (369 μl, 3.36 mmol) in THF (8 mL) was added ECF (2201 μl, 2.3 mmol) and stirred vigorously. After 2 min. a solution of 1-amino-3-propyl alcohol (220 mg, 2.68 mmol) in THF (2 mL) was added to it followed by NMM (505 mg, 5 mmol) and stirred for further 30 minutes. The mixture was warmed to r.t. and stirred for 8 h. The solvent was removed under reduced pressure to give a residue which was diluted with EtOAc and washed with saturated citric acid, saturated NaHCO3 and the organic layer was dried over Na2SO4 and concentrated under vacuum to give a residue, which was purified by silica gel flash column chromatography (EtOAc:MeOH—50:1) to give the desired product as a thick oil in good yields (633 mg, 80%). TLC (MeOH:DCM—1:4; Rf—0.5).

Workup

  1. stirringstirred for further 30 minutes
  2. stirringstirred for 8 h
  3. customThe solvent was removed under reduced pressure
  4. customto give a residue which
  5. washwashed with saturated citric acid, saturated NaHCO3
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customto give a residue, which
  9. customwas purified by silica gel flash column chromatography (EtOAc:MeOH—50:1)

Sources & evidence

ORD record
ord-3ae7945ee1dc4527bf68762eb3f9c5b4
Source dataset
uspto-grants-2014_09
Patent number
US08835602B2

Reaction notes

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