Trifluoroacetate → HCID 18597437, compound

HRID 1981146Notes

Reaction equation

HRID 1981146 reaction equation
C(OC(NCCSCC(=C=O)[C@@H](C(O)=O)NOC(C)(C)C)=O)C1C=CC=CC=1.C1C2C(=CC=CC=2)C[C@@H](C(OCC)=O)N1.[CH2:44]([O:51][C:52]([NH:54][CH2:55][CH2:56][S:57][CH2:58][CH2:59][C@@H:60]([C:69]([N:71]1[C@H:80]([C:81]([O:83][CH2:84][CH3:85])=[O:82])[CH2:79][C:78]2[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=2)[CH2:72]1)=[O:70])[NH:61]C(OC(C)(C)C)=O)=[O:53])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.FC(F)(F)C([O-])=O>>[CH2:44]([O:51][C:52]([NH:54][CH2:55][CH2:56][S:57][CH2:58][CH2:59][C@@H:60]([C:69]([N:71]1[C@H:80]([C:81]([O:83][CH2:84][CH3:85])=[O:82])[CH2:79][C:78]2[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=2)[CH2:72]1)=[O:70])[NH2:61])=[O:53])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

5

Reactant 4

HCID 84468TrifluoroacetateHCID 113332915912-55-7HCID 18597439HCID 18597439, compound2×HCID 86740061HCID 86740061, compound

Product 1

HCID 18597437HCID 18597437, compound

Procedure

S-(2-Benzyloxycarbonylaminoethyl)-N-tert-butoxy-carbonyl-L-homocysteine (2.14 g., 0.00518 mole) and ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (1.12 g., 0.00545 mole) were coupled via the procedure described in Example 5 to give 2.24 g. (72%) of ethyl N-[S-(2-benzyloxycarbonylaminoethyl)-N-tert-butoxycarbonyl-L-homocysteinyl]-1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (1); an oil. Compound 1 (1.10 g., 0.00183 mole) was stirred for 50 minutes at room temperature with 25 ml of trifluoroacetate acid. Concentration in vacuo gave ethyl N-[S-(2-benzyloxycarbonylaminoethyl)-L-homocysteinyl]1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (2) as a crude orange oil. This intermediate (2) was reductively alkylated with 2-oxo-4-phenylbutyric acid (3.00 g., 0.0068 mole) according to the procedure described in Example 5. After chromatography on an LH-20 column with methanol, 0.30 g. (25%) of ethyl N-[S-(2-benzyloxycarbonylaminoethyl)-N-(1-carboxy-3-phenylpropyl)-L-homocysteinyl]-1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (3) was obtained; a colorless oil.

Workup

  1. customto give 2.24 g
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-60fda9eeff73455783c14471a5ff6f13
Source dataset
uspto-grants-1985_04
Patent number
US04512979

Reaction notes

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