Formic Acid → HCID 58516086, compound

HRID 1672171Notes

Reaction equation

C([O:5][C:6](=O)[N:7]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:8][C@@H:9]([C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])(C)(C)C.C(O)=O.C(OC(=O)C)(=O)C>>[CH2:35]([O:34][N:7]([CH2:8][C@@H:9]([C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)[CH2:18][CH2:17]1)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])[CH:6]=[O:5])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

Reactant 3

HCID 284Formic Acid

HCID 7918Acetic Anhydride

HCID 58516082HCID 58516082, compound

Product 1

HCID 58516086HCID 58516086, compoundYield 52.2%

Procedure

The title product was obtained following the protocol of Example 1 (step c), but starting from tert-butyl(benzyloxy){(2S)-2-[(4-biphenyl-4-ylpiperazin-1-yl)carbonyl]-4-methyl pentyl}carbamate (219 mg, 0.46 mmol) and a preformed mixture of formic acid (875 μL; 23.2 mmol; 50 eq.) and acetic anhydride (220 μl; 2.32 mmol; 5.0 eq.) (mixture formed at 0° C. for 30 min). Purification by column chromatography (Silicagel, gradient from 33% EtOAc up to 50% EtOAc in c-Hex) gave the title product as a white solid (120 mg, 52%). HPLC, Rt: 4.60 min (purity: 99.7%). M+(LC-MS (ESI)): 500.4.

Workup

customPurification by column chromatography (Silicagel, gradient from 33% EtOAc up to 50% EtOAc in c-Hex)

Sources & evidence

ORD record: ord-c3a262fe866544fb9c445870dfd3ecf3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998964B2

Reaction notes

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