Diisopropylethylamine → (S)-4-tert-butoxycarbonylamino-4-[4-(N-hydroxycarbamimidoyl)-benzyl carbamoyl]-butyric acid benzyl ester

HRID 576549Notes

Reaction equation

HRID 576549 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[CH2:10][CH2:11][C@H:12]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:13](=[O:24])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:35][OH:36].CCN(C(C)C)C(C)C>C(O)C>[CH2:1]([O:8][C:9](=[O:33])[CH2:10][CH2:11][C@H:12]([NH:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[C:13](=[O:24])[NH:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22](=[NH:23])[NH:35][OH:36])=[CH:20][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 66994809(S)-4-tert-butoxycarbonylamino-4-(4-cyano-benzylcarbamoyl)-butyric acid benzyl ester

Product 1

HCID 178454209(S)-4-tert-butoxycarbonylamino-4-[4-(N-hydroxycarbamimidoyl)-benzyl carbamoyl]-butyric acid benzyl esterYield 152.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound Q (9.65 g, 20.0 mmol), hydroxylamine hydrochloride (2.10 g, 30.0 mmol) and DIEA (5.22 ml, 30.0 mmol) in ethanol (abs., 150 ml) was refluxed for 6 h. The reaction mixture was allowed to cool to room temperature and stirred for additional 16 h, then the solvents were evaporated in vacuo. The resultant residue was dried in vacuo to provide compound R (14.8 g, yield exceeded quantitative) as yellowish oil. LC-MS [M+H] 485.5 (C25H32N4O6+H, calc: 485.8). Compound R was used without further purification.

Workup

  1. customthe solvents were evaporated in vacuo
  2. dry with materialThe resultant residue was dried in vacuo

Sources & evidence

ORD record
ord-3795c97b62a1439ebbfe08ced131a64b
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

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