Hydrogen Bromide → HCID 178462026, compound

HRID 1252524Notes

Reaction equation

HRID 1252524 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:37]C(OC(C)(C)C)=O)[C:17]([NH:19][C@@H:20]([C@H:24]([NH:26][C@H:27]([C:34]([OH:36])=[O:35])[CH2:28][C:29]1[N:30]=[CH:31][NH:32][CH:33]=1)[CH3:25])[C:21]([OH:23])=[O:22])=[O:18])=O)C1C=CC=CC=1.Br>C(O)(=O)C>[NH2:37][C@@H:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH2:11])[C:17]([NH:19][C@@H:20]([C@H:24]([NH:26][C@H:27]([C:34]([OH:36])=[O:35])[CH2:28][C:29]1[N:30]=[CH:31][NH:32][CH:33]=1)[CH3:25])[C:21]([OH:23])=[O:22])=[O:18]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178462025HCID 178462025, compound

Product 1

HCID 178462026HCID 178462026, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (2S,3R)-2-[[(2S)-6-benzyloxycarbonylamino-2-t-butoxycarbonylaminohexanoyl]amino]-3-[[(1S)-1-carboxy-2 (4-imidazolyl)ethyl]amino]butyric acid (720 mg) and 30% hydrogen bromide in acetic acid (20 ml) was sitrred for 3 hours at room temperature and the mixture was poured into ice-water (40 ml). The aqueous solution was washed with ether and subjected to a column of Dowex 50W x 8 (H+, 15 ml). The column was washed with water and the elution was carried out with 2.8% aqueous ammonia. The object fractions were collected and evaporated in vacuo. The residue was dissolved in water and lyophilized to give (2S,3R)-2-[[(2S)-2,6-diaminohexanoyl]amino]-3-[[(1S)-1-carboxy-2-(4-imidazolyl)ethyl]amino]butyric acid (399 mg) as a pale yellow powder.

Workup

  1. washThe aqueous solution was washed with ether
  2. washThe column was washed with water
  3. washthe elution
  4. customThe object fractions were collected
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-cb7c41277f844ae9bde4dc4b974e69a2
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

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