Sulfamic Acid → HCID 19350001, compound

HRID 1637118Notes

Reaction equation

HRID 1637118 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH2:6][CH:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:17]=1)[C:8]#[C:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4].[S:30](=[O:34])(=[O:33])([OH:32])[NH2:31]>>[CH:10]1([NH:31][S:30](=[O:33])(=[O:32])[OH:34])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[NH2:1][CH2:2][C:3]([NH:5][CH2:6][CH:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:17]=1)[C:8]#[C:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4]

Participants

3

Reactant 2

HCID 5987Sulfamic AcidHCID 19349990HCID 19349990, compound

Product 1

HCID 19350001HCID 19350001, compound

Procedure

A solution of 4-t-butoxycarbonylaminomethylcarbonylamino-3-(3-cyclopentyloxy-4methoxyphenyl)-1-phenyl-1-butyne (290 mg, 0.59 mmol) in CH2Cl2 (5 ml) at 0° was treated with trifluoroacetic acid (4 ml). After 1 hr, all the solvents were evaporated. The residue was partitioned between H2O and Et2O, basified with aqueous NaOH, and the Et2O layer seperated, dried, and the solvent evaporated, and gave 4-aminomethylcarbonylamino-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-phenyl-1-butyne, 200 mg (86%). The salt was formed by treating this amine (180 mg) in Me2CO (2 ml) with sulfamic acid (82 mg). The solution was concentrated to almost dryness, and the resultant crystals were triturated with Me2CO, and gave the titled compound, mp 119-124°. 1H NMR (400 MHz, CDCl3) δ 8.22 (t, 1 H), 7.44 (m, 3 H), 7.28 (m, 3 H), 7.02 (d, 1 H), 6.94 (m, 1 H), 6.82 (d, 1 H), 4.80 (m, 1 H), 4.04 (t, 1 H), 3.80 (s, 3 H), 3.76 (m, 2 H), 3.62 (m, 1 H), 3.52 (m, 1 H), 3.18 (m, 1 H), 2.04 (m, 2 H), 1.80-1.98 (m, 6 H), 1.52-1.72 (m, 4 H), 1.08-1.32 (m, 6 H).

Workup

  1. customThe salt was formed
  2. concentrationThe solution was concentrated to almost dryness
  3. customthe resultant crystals were triturated with Me2CO

Sources & evidence

ORD record
ord-843a36d7347043b7947bab225dc6e05f
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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