N-(tert-Butoxycarbonyl)-L-tryptophyl-L-methioninamide → HCID 13306579, compound

HRID 2412321Notes

Reaction equation

HRID 2412321 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH2:23])=[O:22])[CH2:17][CH2:18][S:19][CH3:20])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.CO.CCOC(C)=O>C(O)=O>[NH2:1][C@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH2:23])=[O:22])[CH2:17][CH2:18][S:19][CH3:20])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

4

Reactant 2

HCID 13306577N-(tert-Butoxycarbonyl)-L-tryptophyl-L-methioninamideHCID 21584119Ethylacetate methanol

Product 1

HCID 13306579HCID 13306579, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A 3.911 g (9 mmol) amount of Boc-Trp-Met-NH2 (I) was dissolved in 40 ml of formic acid at room temperature. After complete Boc-removal (TLC monitoring) the solvent was evaporated in vacuo at 30° C. The residue was dissolved in methanol cooled to 0° C., and 3.6 ml (10.8 mmol) of a 3M solution of hydrogen chloride in anhydrous tetrahydrofuran were added. Solvents were removed in vacuo, and 3 g (90% yield) of compound II were obtained from MeOH/AcOEt: m.p. 114° C. (D); [α]D20 =+20.4° (c=1 MeOH): RfC 0.62; E1.2 0.82.

Workup

  1. customAfter complete Boc-removal (TLC monitoring) the solvent
  2. customwas evaporated in vacuo at 30° C
  3. dissolutionThe residue was dissolved in methanol
  4. addition3.6 ml (10.8 mmol) of a 3M solution of hydrogen chloride in anhydrous tetrahydrofuran were added
  5. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-8f6049e8b70b4a148d56ae5e55392bc8
Source dataset
uspto-grants-1985_01
Patent number
US04491541

Reaction notes

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