Triethylamine → HCID 59201592, compound

HRID 451818Notes

Reaction equation

HRID 451818 reaction equation
Cl.[NH2:2][CH2:3][C@@H:4]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:5]([O:7][CH3:8])=[O:6].CCN(CC)CC.[Cl:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32]>CO>[CH2:13]([O:12][C:10]([NH:9][C@H:4]([CH2:3][NH:2][C:31](=[O:32])[CH2:30][CH2:29][CH2:28][Cl:27])[C:5]([O:7][CH3:8])=[O:6])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 13756826Z-D-Dap-OMe.HCl

Product 1

HCID 59201592HCID 59201592, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R)-methyl 3-amino-2-(benzyloxycarbonylamino)propanoate hydrochloride (4.0 g, 0.014 mol) in methanol (80 mL) was cooled to 0° C. To this mixture was added Et3N (3.3 g, 31 mmol), followed by 4-chlorobutanoyl chloride (2.3 g, 15.0 mmol). The reaction mixture was allowed to warm to rt and stirred for 4 h. The reaction was quenched with saturated brine (200 mL), the organic layer extracted with CH2Cl2, washed with 1N HCl, saturated brine, dried over MgSO4 and concentrated to give crude (R)-methyl 2-(benzyloxycarbonylamino)-3-(4-chlorobutanamido)propanoate (5.0 g) that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 7.45-7.35 (m, 5H) 6.01 (s, 1H), 5.84 (d, 1H), 5.11 (d, 2H), 4.42 (t, 5H), 3.68-3.50 (m, 6H), 2.32 (t, 2H), 2.08 (t, 2H).

Workup

  1. customThe reaction was quenched with saturated brine (200 mL)
  2. extractionthe organic layer extracted with CH2Cl2
  3. washwashed with 1N HCl, saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-de62f20a7cb840f68f0a63bad0ed282e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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