Trifluoroacetic acid → HCID 53789842, compound

HRID 1583984Notes

Reaction equation

[C:1]([OH:7])(C(F)(F)F)=[O:2].O=C(C[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C(OCC)=O.C([BH3-])#N.[Na+].Br.CC(O)=O.C(OC(C([NH:46][C@H:47]([C:56]([N:58]1[CH2:65][CH2:64][CH2:63][C@H:59]1[C:60]([OH:62])=[O:61])=[O:57])[CH2:48][CH2:49][CH2:50][NH:51][C:52](=[O:55])[CH2:53][NH2:54])CCC1C=CC=CC=1)=O)C>>[C:1]([NH:54][CH2:53][C:52]([NH:51][CH2:50][CH2:49][CH2:48][C@@H:47]([C:56]([N:58]1[CH2:65][CH2:64][CH2:63][C@H:59]1[C:60]([OH:62])=[O:61])=[O:57])[NH2:46])=[O:55])([O:7][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:2]

Participants

Reactant 5

HCID 6422Trifluoroacetic acid

HCID 562087Ethyl alpha-oxobenzenebutanoate

HCID 5003444Sodium cyanoborohydride

HCID 13605255HCID 13605255, compound

HCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 53789842HCID 53789842, compound

Procedure

N-[N5 -(N-Cbz-glycyl)-L-ornithyl]-L-proline was prepared as described in Example 4. The reductive alkylation of TFA salt (132 mg, 0.314 mmol) with ethyl 2-oxo-4-phenylbutyrate (324 mg, 1.57 mmol) and sodium cyanoborohydride (59.2 mg, 0.942 mmol) was carried out in the usual manner. The work up, including 30-32% HBr/HOAc treatment, was the same as that described in Example 1. Both ms and nmr were consistent with the structure for N-[N2 -(1-ethoxycarbonyl-3-phenylpropyl)-N5 -glycyl-L-ornithyl]-L-proline (47.5 mg).

Sources & evidence

ORD record: ord-c1955ce8ada94351b1d4180a47354b99
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04555502

Reaction notes

Loading…