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4-Methylmorpholine → Boc-(D)-Met-(L)-Ala-OMe

HRID 1263415
Notes
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Reaction equation

HRID 1263415 reaction equation
CN1CCOCC1.Cl.[CH3:9][O:10][C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13].C1C=CC2N(O)N=NC=2C=1.[C:26]([NH:33][C@@H:34]([C:39](O)=[O:40])[CH2:35][CH2:36][S:37][CH3:38])([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>CN(C=O)C>[NH:33]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@@H:34]([C:39]([NH:13][C@H:12]([C:11]([O:10][CH3:9])=[O:15])[CH3:14])=[O:40])[CH2:35][CH2:36][S:37][CH3:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 111051N-(tert-Butyloxycarbonyl)-D-methionineHCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 11024115Boc-(D)-Met-(L)-Ala-OMeYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

N-methylmorpholine (5.6 g), L-alanine methyl ester hydrochloride (3.9 g), HOBt (4.6 g) and 1-(3-dimethlylaminopropyl)-3-ethylcarbodiimide (5.3 g) was added to a solution of Boc-(D)-Methionine (7 g, 0.028 mol) in dry DMF (50 ml). The mixture was stirred overnight. Solvent was removed by evaporation and the residue was partitioned between dichloromethane (100 ml) and 5% aqueous acetic acid (5 ml). On standing HOBt crystallised and was removed by filtration, and the organic layer was separated and washed with aqueous sodium bicarbonate, dried (MgSO4) and evaporated. The residue (8.5 g) was purified by flash chromatography in a sinter funnel eluting with a mixture of dichloromethane and ether (0% to 100% ether). The fractions containing product were combined and evaporated to give Boc-(D)-Met-(L)-Ala-OMe (7.2 g) as a gum which crystallised on standing; NMR (CDCl3): 1.4 (d, 3H), 1.45 (s, 9H), 1.95 (m, 1H), 2.1 (s, 3H), 2.1 (m, 1H), 2.6 (m, 2H), 3.75 (s, 3H), 4.3 (bs, 1H), 4.6 (m, 1H), 5.3 (m, 1H), 6.9 (bs, 1H).

Workup

  1. customSolvent was removed by evaporation
  2. customthe residue was partitioned between dichloromethane (100 ml) and 5% aqueous acetic acid (5 ml)
  3. customcrystallised
  4. customwas removed by filtration
  5. customthe organic layer was separated
  6. washwashed with aqueous sodium bicarbonate
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue (8.5 g) was purified by flash chromatography in a sinter funnel
  10. washeluting with a mixture of dichloromethane and ether (0% to 100% ether)
  11. additionThe fractions containing product
  12. customevaporated

Sources & evidence

ORD record
ord-82271cd3d2984981b7feacd21c9f6148
Source dataset
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06541453B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes