Methanol → HCID 68604642, compound

HRID 1593273Notes

Reaction equation

HRID 1593273 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:17]([S:24][CH2:25][CH2:26][NH:27]C(OC(C)(C)C)=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C(Cl)(=O)C.CCOCC>C(OCC)(=O)C>[NH2:27][CH2:26][CH2:25][S:24][CH:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 68605304Methyl 2-{[(benzyloxy)carbonyl]amino}-3-({2-[(tert-butoxycarbonyl)amino]ethyl}thio)-3-phenylpropanoate

Product 1

HCID 68604642HCID 68604642, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred cooled (ice-bath) solution of methyl 2-{[(benzyloxy)carbonyl]amino}-3-({2-[(tert-butoxycarbonyl)amino]ethyl}thio)-3-phenylpropanoate (7a) (1.20 g) and methanol (0.284 mL) in ethyl acetate (2 mL) was added dropwise from a syringe acetyl chloride (0.43 mL) and the mixture stirred in the ice bath for an additional 10 min and then at RT for 50 min. Excess Et2O was added and the white solid collected, dissolved in water, treated with an excess of sat. aqueous K2CO3 and extracted once with CH2Cl2 and twice with Et2O. The dried organics (MgSO4) were filtered and the solvent removed to yield the title compound as an oil (0.86 g, 90%). The proton NMR displayed a mixture of diastereomers of approximate ratio 7:3; the major diastereomer is reported. 1H NMR (300 MHz, CDCl3) δ1.46 (s, 2H, exchangeable), 2.47 (t, 2H), 2.76 (t, 2H), 3.66 (s, 3H), 3.35 (d, 1H), 4.75 (t, 1H), 5.09 (m, 2H), 5.76 (d, 1H, exchangeable), 7.28-7.34 (m, 10H). MS APCI, m/z=389(M+1). HPLC Method A: 2.27 min.

Workup

  1. customthe white solid collected
  2. dissolutiondissolved in water
  3. additiontreated with an excess of sat. aqueous K2CO3
  4. extractionextracted once with CH2Cl2 and twice with Et2O
  5. filtrationThe dried organics (MgSO4) were filtered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-6728923efee1447890b3d8afd2b2a014
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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