Formic Acid → HCID 58516086, compound

HRID 1875717Notes

Reaction equation

[CH2:1]([O:8][N:9]([CH2:17][C@@H:18]([C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])[C:10](=O)[O:11]C(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=O.C(OC(=O)C)(=O)C>>[CH2:1]([O:8][N:9]([CH2:17][C@@H:18]([C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:32]=[CH:33][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:35][CH:36]=2)[CH2:27][CH2:26]1)=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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-18a11bb2f1d04350af3a223fc2d64c93
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309579B2

Reaction notes

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